1,4-Addition of diorganozincs to α,β-unsaturated ketones catalyzed by a copper(I)-sulfonamide combined system

Bulletin of the Chemical Society of Japan

Volumn 73, Issue 4, 2000, Pages 999-1014

  Kitamura, Masato ^a   Miki, Takashi ^a   Nakano, Keiji ^a   Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; ZINC;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; GEOMETRY; ORGANIC CHEMISTRY; QUANTITATIVE DIAGNOSIS; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0034016091     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.73.999     Document Type: Article

References (171)

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2. Reviews: P. Perlmutter, "Conjugate Addition Reactions in Organic Synthesis," Pergamon Press, Oxford (1992); V. J. Lee, "Conjugate Additions of Reactive Carbanions to Activated Alkenes and Alkynes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 69; V. J. Lee, "Conjugate Additions of Carbon Ligands to Activated Alkenes and Alkynes Mediated by Lewis Acids," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 139.
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4. M. J. Chapdelaine and M. Hulce, "Tandem Vicinal Difunctionalization: β-Addition to α,β-Unsaturated Carbonyl Substrates Followed by α-Functionalization," in "Organic Reactions," ed by L. A. Paquette, John Wiley & Sons, New York (1990), Vol. 38, p. 225.
5. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
6. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
7. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
8. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
9. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
10. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
11. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
12. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
13. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
14. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
15. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
16. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
17. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
18. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
19. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
20. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
21. 3SiCl-Accelerated Conjugate Addition Reactions of Organocopper Reagents," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 6. h) T. Ibuka and Y. Yamamoto, "Boron Trifluoride/Aluminum Trichloride-Mediated Conjugate Addition and Substitution Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 7. i) M. Suzuki and R. Noyori, "Conjugate Addition-Enolate-Trapping Reactions," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 9. j) J.-F. Normant, "Alkyne Carbocupration and Polyene Synthesis," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 11. k) J. A. Kozlowski, "Organocuprates in the Conjugate Addition Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 169. l) E. Nakamura, Synlett, 1991, 539. m) S. H. Bertz and G. Dabbagh, Tetrahedron, 45, 425 (1989). n) G. H. Posner, "An Introduction to Synthesis Using Organocopper Reagents," John Wiley & Sons, New York (1980). See also: o) S. H. Bertz, M. Eriksson, G. Miao, and J. P. Snyder, J. Am. Chem. Soc., 118, 10906 (1996). p) H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). q) H. Gilman, R. G. Jones, and L. A. Woods, J. Org. Chem., 17, 1630 (1952).
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32. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
33. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
34. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
35. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
36. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
37. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
38. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
39. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
40. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami,
41. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
42. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
43. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
44. Cu(I)-catalyzed 1,4-addition of organometallics. Li: a) J. Green and S. Woodward, Synlett, 1995, 155. Mg: b) M. T. Reetz and A. Kindler, J. Organomet. Chem., 502, C5 (1995). c) H. O. House, R. A. Latham, and C. D. Slater, J. Org. Chem., 31, 2667 (1966). d) F. S. Prout and M. M. E. Abdulslam, J. Chem. Eng. Data, 11, 616 (1966). e) A. J. Birch and M. Smith, Proc. Chem. Soc., 1962, 356. A1: f) J. Kabbara, S. Flemming, K. Nickisch, H. Neh, and J. Westermann, Tetrahedron, 51, 743 (1995). g) P. Wipf, J. H. Smitrovich, and C.-W. Moon, J. Org. Chem., 57, 3178 (1992). Zn: h) A. Alexakis, J. Vestra, and P. Mangeney, Tetrahedron Lett., 38, 7745 (1997). Ti: i) M. Arai, E. Nakamura, and B. H. Lipshutz, J. Org. Chem., 56, 5489 (1991). Zr: j) B. H. Lipshutz and M. Segi, Tetrahedron, 51, 4407 (1995); k) P. Wipf, W. Xu, J. H. Smitrovich, R. Lehmann, and L. M. Venanzi, Tetrahedron, 50, 1935 (1994). Mn: l) G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989). For Cu(II)-catalyzed reaction, see: m) H. Sakata, Y. Aoki, and I. Kuwajima, Tetrahedron Lett., 31, 1161 (1990).
45. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
46. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
47. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
48. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
49. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
50. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
51. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
52. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
53. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
54. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
55. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
56. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
57. 3: B. H. Lipshutz and M. R. Wood, J. Am. Chem. Soc., 116, 11689 (1994). Conjugate addition of alkyl halides in the presence of Zn/Cu couple: C. Petrier, C. Dupuy, and J. L. Luche, Tetrahedron Lett., 27, 3149 (1986). For the stoichiometric reaction using Li/Zn/Cu mixed reagents: M. J. Rozema, A. Sidduri, and P. Knochel, J. Org. Chem., 57, 1956 (1992); L. Zhu, R. M. Wehmeyer, and R. D. Rieke, J. Org. Chem., 56, 1445 (1991). For the acceleration effect of chlorotrimethylsilane on the 1, 4-addition reaction of lithium diorganocuprates, see: C. R. Johnson and T. Marren, Tetrahedron Lett., 28, 27 (1987); E. Nakamura, S. Matsuzawa, Y. Horiguchi, and I. Kuwajima, Tetrahedron Lett., 27, 4029 (1986); A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett., 27, 1047 (1986); E. J. Corey and N. W. Boaz, Tetrahedron Lett., 26, 6019 (1985); C. Chuit, J. P. Foulon, and J. F. Normant, Tetrahedron, 36, 2305 (1980).
58. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
59. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
60. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
61. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
62. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
63. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
64. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
65. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
66. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
67. Y. Morita, M. Suzuki, and R. Noyori, J. Org. Chem., 54, 1785 (1989); J. F. G. A. Jansen and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1989, 741. For the 1,4-addition of Li/Zn or Mg/Zn mixed reagents, see: M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori, Tetrahedron, 46, 4809 (1990); T. Takahashi, M. Nakazawa, M. Kanoh, and K. Yamamoto, Tetrahedron Lett., 31, 7349 (1990); M. Suzuki, H. Koyano, Y. Morita, and R. Noyori, Synlett, 1989, 22; R. A. Kjonaas and R. K. Hoffer, J. Org. Chem., 53, 4133 (1988); W. Tückmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986); M. Isobe, S. Kondo, N. Nagasawa, and T. Goto, Chem. Lett., 1977, 679. Application to the prostaglandins synthesis: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 6; M. Suzuki, A. Yanagisawa, and R. Noyori, J. Am. Chem. Soc., 110, 4718 (1988).
68. M. S. Kharasch and P. O. Tawney, J. Am. Chem. Soc., 63, 2308 (1941).
69. Preliminary communication: M. Kitamura, T. Miki, K. Nakano, and R. Noyori, Tetrahedron Lett., 37, 5141 (1996).
70. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
71. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
72. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
73. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
74. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
75. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
76. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
77. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
78. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
79. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
80. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
81. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
82. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
83. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
84. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
85. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
86. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
87. For the mechanistic studies on Cu-based 1,4-addition, see: D. E. Frantz, D. A. Singleton, and J. P. Snyder, J. Am. Chem. Soc., 119, 3383 (1997); M. Eriksson, A. Johansson, M. Nilsson, and T. Olsson, J. Am. Chem. Soc., 118, 10904 (1996); S. H. Bertz, G. Miao, B. E. Rossiter, and J. P. Snyder, J. Am. Chem. Soc., 117, 11023 (1995); A. S. Vellekoop and R. A. J. Smith, J. Am. Chem. Soc., 116, 2902 (1994); N. Krause, R. Wagner, and A. Gerold, J. Am. Chem. Soc., 116, 381 (1994); B. H. Lipshutz, S. H. Dimock, and B. James, J. Am. Chem. Soc., 115, 9283 (1993); E. J. Corey, F. J. Hannon, and N. W. Boaz, Tetrahedron, 45, 545 (1989); Y. Horiguchi, M. Kamatsu, and I. Kuwajima, Tetrahedron Lett., 30, 7087 (1989); C. Ullenius and B. Christenson, Pure Appl. Chem., 60, 57 (1988); S. R. Krauss and S. G. Smith, J. Am. Chem. Soc., 103, 141 (1981); J. Berlan, J.-P. Battioni, and K. Koosha, Bull. Soc. Chim. Fr. II, 1979, 183; H. O. House, Acc. Chem. Res., 9, 59 (1976); C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 95, 7783 (1973). Molecular orbital calculation on the transition structures for the conjugate addition of organocopper reagents: S. Mori and K. Morokuma, Chem. Eur. J., 5, 1534 (1999); E. Nakamura, S. Mori, and K. Morokuma, J. Am. Chem. Soc., 119, 4900 (1997); B. H. Lipshutz, D. H. Aue, and B. James, Tetrahedron Lett., 37, 8471 (1996); J. P. Snyder, J. Am. Chem. Soc., 117, 11025 (1995); A. E. Dorigo and K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989).
88. J. Boersma, "Zinc and Cadmium," in "Comprehensive Organometallic Chemistry," ed by G. Wilkinson, F. G. A. Stone, and E. W. Abel, Pergamon Press, New York (1982), Vol. 2, Chap. 16.
89. a) F. H. van der Steen, J. Boersma, A. L. Spek, and G. van Koten, Organometallics, 10, 2467 (1991).
90. b) M. M. Hansen, P. A. Bartlett, and C. H. Heathcock, Organometallics, 6, 2069 (1987).
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92. "Handbook of Chemistry and Physics," 70th ed, 1989-1990, ed by R. C. Weast, CRC Press, Boca Raton (1989), p. D-151.
93. 8h The discrepancy may be due to the purity of diethylzinc, CuCN, or 2-cyclohexenone. The purity of diethylzinc profoundly influences the reactivity.
94. M. F. N. N. Carvalho, A. C. Consiglieri, M. T. Duarte, A. M. Galvão, A. J. L. Pombeiro, and R. Herrmann, Inorg. Chem., 32, 5160 (1993); E. J. Corey, S. Sarshar, and J. Bordner, J. Am. Chem. Soc., 114, 7938 (1992); F. A. Cotton and P. F. Stokely, J. Am. Chem. Soc., 92, 294 (1970); J. Moréno
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96. M. F. N. N. Carvalho, A. C. Consiglieri, M. T. Duarte, A. M. Galvão, A. J. L. Pombeiro, and R. Herrmann, Inorg. Chem., 32, 5160 (1993); E. J. Corey, S. Sarshar, and J. Bordner, J. Am. Chem. Soc., 114, 7938 (1992); F. A. Cotton and P. F. Stokely, J. Am. Chem. Soc., 92, 294 (1970); J. Moréno and M. Alléaume, Compt. Rend., C267, 64 (1968).
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104. The mixed-metal enolate might induce side reactions facilely.
105. Some metal or mixed-metal enolates can be allylated in high yield by using Pd complexes as catalysts. Si: J. Tsuji, I. Minami, and I. Shimizu, Chem. Lett., 1983, 1325. Sn: B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2591 (1980). B/Li: F.-T. Luo and E. Negishi, Tetrahedron Lett., 26, 2177 (1985). B/K: E. Negishi, H. Matsushita, S. Chatterjee, and R. A. John, J. Org. Chem., 47, 3188 (1982). Zn/Li: E. Negishi and R. A. John, J. Org. Chem., 48, 4098 (1983).
106. Some metal or mixed-metal enolates can be allylated in high yield by using Pd complexes as catalysts. Si: J. Tsuji, I. Minami, and I. Shimizu, Chem. Lett., 1983, 1325. Sn: B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2591 (1980). B/Li: F.-T. Luo and E. Negishi, Tetrahedron Lett., 26, 2177 (1985). B/K: E. Negishi, H. Matsushita, S. Chatterjee, and R. A. John, J. Org. Chem., 47, 3188 (1982). Zn/Li: E. Negishi and R. A. John, J. Org. Chem., 48, 4098 (1983).
107. Some metal or mixed-metal enolates can be allylated in high yield by using Pd complexes as catalysts. Si: J. Tsuji, I. Minami, and I. Shimizu, Chem. Lett., 1983, 1325. Sn: B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2591 (1980). B/Li: F.-T. Luo and E. Negishi, Tetrahedron Lett., 26, 2177 (1985). B/K: E. Negishi, H. Matsushita, S. Chatterjee, and R. A. John, J. Org. Chem., 47, 3188 (1982). Zn/Li: E. Negishi and R. A. John, J. Org. Chem., 48, 4098 (1983).
108. Some metal or mixed-metal enolates can be allylated in high yield by using Pd complexes as catalysts. Si: J. Tsuji, I. Minami, and I. Shimizu, Chem. Lett., 1983, 1325. Sn: B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2591 (1980). B/Li: F.-T. Luo and E. Negishi, Tetrahedron Lett., 26, 2177 (1985). B/K: E. Negishi, H. Matsushita, S. Chatterjee, and R. A. John, J. Org. Chem., 47, 3188 (1982). Zn/Li: E. Negishi and R. A. John, J. Org. Chem., 48, 4098 (1983).
109. Some metal or mixed-metal enolates can be allylated in high yield by using Pd complexes as catalysts. Si: J. Tsuji, I. Minami, and I. Shimizu, Chem. Lett., 1983, 1325. Sn: B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2591 (1980). B/Li: F.-T. Luo and E. Negishi, Tetrahedron Lett., 26, 2177 (1985). B/K: E. Negishi, H. Matsushita, S. Chatterjee, and R. A. John, J. Org. Chem., 47, 3188 (1982). Zn/Li: E. Negishi and R. A. John, J. Org. Chem., 48, 4098 (1983).
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112. H. K. Hofstee, J. Boersma, and G. J. M. van der Kerk, J. Organomet. Chem., 144, 255 (1978); K.-H. Thiele and J. Köhler, J. Organomet. Chem., 12, 225 (1968).
113. 3p
114. S. Shambayati and S. L. Schreiber, "Lewis Acid Carbonyl Complexation," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 283.
115. P. R. Markies, G. Schat, O. S. Akkerman, F. Bikelhaupt, W. J. J. Smeeta, and A. L. Spek, Organometallics, 9, 2243 (1990); E. Weiss and R. Wolfrum, Chem. Ber., 101, 35 (1968).
116. P. R. Markies, G. Schat, O. S. Akkerman, F. Bikelhaupt, W. J. J. Smeeta, and A. L. Spek, Organometallics, 9, 2243 (1990); E. Weiss and R. Wolfrum, Chem. Ber., 101, 35 (1968).
117. R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991); M. Kitamura, S. Okada, S. Suga, and R. Noyori, J. Am. Chem. Soc., 111, 4028 (1989); M. Kitamura, S. Suga, K. Kawai, and R. Noyori, J. Am. Chem. Soc., 108, 6071 (1986). Theoretical support: M. Yamakawa and R. Noyori, Organometallics, 18, 128 (1999); M. Yamakawa and R. Noyori, J. Am. Chem. Soc., 117, 6327 (1995).
118. R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991); M. Kitamura, S. Okada, S. Suga, and R. Noyori, J. Am. Chem. Soc., 111, 4028 (1989); M. Kitamura, S. Suga, K. Kawai, and R. Noyori, J. Am. Chem. Soc., 108, 6071 (1986). Theoretical support: M. Yamakawa and R. Noyori, Organometallics, 18, 128 (1999); M. Yamakawa and R. Noyori, J. Am. Chem. Soc., 117, 6327 (1995).
119. R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991); M. Kitamura, S. Okada, S. Suga, and R. Noyori, J. Am. Chem. Soc., 111, 4028 (1989); M. Kitamura, S. Suga, K. Kawai, and R. Noyori, J. Am. Chem. Soc., 108, 6071 (1986). Theoretical support: M. Yamakawa and R. Noyori, Organometallics, 18, 128 (1999); M. Yamakawa and R. Noyori, J. Am. Chem. Soc., 117, 6327 (1995).
120. R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991); M. Kitamura, S. Okada, S. Suga, and R. Noyori, J. Am. Chem. Soc., 111, 4028 (1989); M. Kitamura, S. Suga, K. Kawai, and R. Noyori, J. Am. Chem. Soc., 108, 6071 (1986). Theoretical support: M. Yamakawa and R. Noyori, Organometallics, 18, 128 (1999); M. Yamakawa and R. Noyori, J. Am. Chem. Soc., 117, 6327 (1995).
121. R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991); M. Kitamura, S. Okada, S. Suga, and R. Noyori, J. Am. Chem. Soc., 111, 4028 (1989); M. Kitamura, S. Suga, K. Kawai, and R. Noyori, J. Am. Chem. Soc., 108, 6071 (1986). Theoretical support: M. Yamakawa and R. Noyori, Organometallics, 18, 128 (1999); M. Yamakawa and R. Noyori, J. Am. Chem. Soc., 117, 6327 (1995).
122. I. G. Dance, P. A. W. Dean, and K. J. Fisher, Inorg. Chem., 33, 6261 (1994); B. F. Hoskins and R. Robson, J. Am. Chem. Soc., 112, 1546 (1990); C. Kappenstein and U. Schubert, J. Chem. Soc., Chem. Commun., 1980, 1116; D. T. Cromer, A. C. Larson, and R. B. Roof, Jr., Acta Crystallogr., 19, 192 (1965).
123. I. G. Dance, P. A. W. Dean, and K. J. Fisher, Inorg. Chem., 33, 6261 (1994); B. F. Hoskins and R. Robson, J. Am. Chem. Soc., 112, 1546 (1990); C. Kappenstein and U. Schubert, J. Chem. Soc., Chem. Commun., 1980, 1116; D. T. Cromer, A. C. Larson, and R. B. Roof, Jr., Acta Crystallogr., 19, 192 (1965).
124. I. G. Dance, P. A. W. Dean, and K. J. Fisher, Inorg. Chem., 33, 6261 (1994); B. F. Hoskins and R. Robson, J. Am. Chem. Soc., 112, 1546 (1990); C. Kappenstein and U. Schubert, J. Chem. Soc., Chem. Commun., 1980, 1116; D. T. Cromer, A. C. Larson, and R. B. Roof, Jr., Acta Crystallogr., 19, 192 (1965).
125. I. G. Dance, P. A. W. Dean, and K. J. Fisher, Inorg. Chem., 33, 6261 (1994); B. F. Hoskins and R. Robson, J. Am. Chem. Soc., 112, 1546 (1990); C. Kappenstein and U. Schubert, J. Chem. Soc., Chem. Commun., 1980, 1116; D. T. Cromer, A. C. Larson, and R. B. Roof, Jr., Acta Crystallogr., 19, 192 (1965).
126. C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 120, 9688 (1998), and references cited therein. See also: S. H. Bertz, K. Nilsson, O. Davidsson, and J. P. Snyder, Angew. Chem., Int. Ed. Engl., 37, 314 (1998); J. A. Cabezas and A. C. Oehlschlager, J. Am. Chem. Soc., 119, 3878 (1997); S. H. Bertz, G. Miao, and M. Eriksson, Chem. Commun., 1996, 815; T. L. Stemmler, T. M. Barnhart, J. E. Penner-Hahn, C. E. Tucker, P. Knochel, M. Böhme, and G. Frenking, J. Am. Chem. Soc., 117, 12489 (1995); B. H. Lipshutz and B. James, J. Org. Chem., 59, 7585 (1994).
127. C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 120, 9688 (1998), and references cited therein. See also: S. H. Bertz, K. Nilsson, O. Davidsson, and J. P. Snyder, Angew. Chem., Int. Ed. Engl., 37, 314 (1998); J. A. Cabezas and A. C. Oehlschlager, J. Am. Chem. Soc., 119, 3878 (1997); S. H. Bertz, G. Miao, and M. Eriksson, Chem. Commun., 1996, 815; T. L. Stemmler, T. M. Barnhart, J. E. Penner-Hahn, C. E. Tucker, P. Knochel, M. Böhme, and G. Frenking, J. Am. Chem. Soc., 117, 12489 (1995); B. H. Lipshutz and B. James, J. Org. Chem., 59, 7585 (1994).
128. C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 120, 9688 (1998), and references cited therein. See also: S. H. Bertz, K. Nilsson, O. Davidsson, and J. P. Snyder, Angew. Chem., Int. Ed. Engl., 37, 314 (1998); J. A. Cabezas and A. C. Oehlschlager, J. Am. Chem. Soc., 119, 3878 (1997); S. H. Bertz, G. Miao, and M. Eriksson, Chem. Commun., 1996, 815; T. L. Stemmler, T. M. Barnhart, J. E. Penner-Hahn, C. E. Tucker, P. Knochel, M. Böhme, and G. Frenking, J. Am. Chem. Soc., 117, 12489 (1995); B. H. Lipshutz and B. James, J. Org. Chem., 59, 7585 (1994).
129. C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 120, 9688 (1998), and references cited therein. See also: S. H. Bertz, K. Nilsson, O. Davidsson, and J. P. Snyder, Angew. Chem., Int. Ed. Engl., 37, 314 (1998); J. A. Cabezas and A. C. Oehlschlager, J. Am. Chem. Soc., 119, 3878 (1997); S. H. Bertz, G. Miao, and M. Eriksson, Chem. Commun., 1996, 815; T. L. Stemmler, T. M. Barnhart, J. E. Penner-Hahn, C. E. Tucker, P. Knochel, M. Böhme, and G. Frenking, J. Am. Chem. Soc., 117, 12489 (1995); B. H. Lipshutz and B. James, J. Org. Chem., 59, 7585 (1994).
130. C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 120, 9688 (1998), and references cited therein. See also: S. H. Bertz, K. Nilsson, O. Davidsson, and J. P. Snyder, Angew. Chem., Int. Ed. Engl., 37, 314 (1998); J. A. Cabezas and A. C. Oehlschlager, J. Am. Chem. Soc., 119, 3878 (1997); S. H. Bertz, G. Miao, and M. Eriksson, Chem. Commun., 1996, 815; T. L. Stemmler, T. M. Barnhart, J. E. Penner-Hahn, C. E. Tucker, P. Knochel, M. Böhme, and G. Frenking, J. Am. Chem. Soc., 117, 12489 (1995); B. H. Lipshutz and B. James, J. Org. Chem., 59, 7585 (1994).
131. C. M. P. Kronenburg, J. T. B. H. Jastrzebski, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 120, 9688 (1998), and references cited therein. See also: S. H. Bertz, K. Nilsson, O. Davidsson, and J. P. Snyder, Angew. Chem., Int. Ed. Engl., 37, 314 (1998); J. A. Cabezas and A. C. Oehlschlager, J. Am. Chem. Soc., 119, 3878 (1997); S. H. Bertz, G. Miao, and M. Eriksson, Chem. Commun., 1996, 815; T. L. Stemmler, T. M. Barnhart, J. E. Penner-Hahn, C. E. Tucker, P. Knochel, M. Böhme, and G. Frenking, J. Am. Chem. Soc., 117, 12489 (1995); B. H. Lipshutz and B. James, J. Org. Chem., 59, 7585 (1994).
132. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
133. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
134. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
135. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
136. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
137. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
138. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
139. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
140. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
141. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
142. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
143. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
144. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
145. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
146. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
147. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
148. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
149. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
150. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K.
151. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
152. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
153. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
154. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
155. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
156. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
157. Reviews: B. L. Feringa and A. H. M. de Vries, "Advances in Catalytic Process," ed by M. D. Doyle, JAI Press, Connecticut (1995), Vol. 1, p. 151; R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994), Chap. 4; A. Alexakis, "Asymmetric Conjugate Addition," in "Organocopper Reagents," ed by R. J. K. Taylor, Oxford University Press, Oxford (1994), Chap. 8; B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992); H.-G. Schmalz, "Asymmetric Nucleophilic Addition to Electron Deficient Alkenes," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p. 199. Co-catalyzed asymmetric 1,4-addition: A. H. M. de Vries and B. L Feringa, Tetrahedron: Asymmetry, 8, 1377 (1997). Rh-catalyzed asymmetric 1,4-addition: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura, J. Am. Chem. Soc., 120, 5579 (1998). Ni-catalyzed asymmetric 1,4-addition: A. H. M. de Vries, R. Imbos, and B. L Feringa, Tetrahedron: Asymmetry, 8, 1467 (1997); C. L. Gibson, Tetrahedron: Asymmetry, 7, 3357 (1996); M. Asami, K. Usui, S. Higuchi, and S. Inoue, Chem. Lett., 1994, 297; A. Corma, M. Iglesias, M. V. Martin, J. Rubio, and F. Sánchez, Tetrahedron: Asymmetry, 3, 845 (1992); M. Uemura, R. Miyake, K. Nakayama, and Y. Hayashi, Tetrahedron: Asymmetry, 3, 713 (1992); C. Bolm and M. Ewald, Tetrahedron Lett., 31, 5011 (1990); K. Soai, T. Hayasaka, and S. Ugajin, J. Chem. Soc., Chem. Commun., 1989, 516. Cu-catalyzed asymmetric 1,4-addition: O. Pàmies, G. Net, A. Ruiz, and C. Claver, Tetrahedron: Asymmetry, 10, 2007 (1999); M. Yan, L.-W. Yang, K.-Y. Wong, and A. S. C. Chan, Chem. Commun., 1999, 11; Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka, Tetrahedron, 54, 10295 (1998); B. L Feringa, M. Pineschi, L. A. Arnold, R. Imbos, and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 36, 2620 (1997); A. K. H. Knöbel, I. H. Escher, and A. Pfaltz, Synlett, 1997, 1429; A. Alexakis, J. Vestra, J. Burton, and P. Mangeney, Tetrahedron: Asymmetry, 8, 3193 (1997); V. Wendisch and N. Sewald, Tetrahedron: Asymmetry, 8, 1253 (1997); M. Kanai and K. Tomioka, Tetrahedron Lett., 36, 4275 (1995); M. Spescha and G. Rihs, Helv. Chim. Acta, 76, 1219 (1993); D. M. Knotter, D. M. Grove, W. J. J. Smeets, A. L. Spek, and G. van Koten, J. Am. Chem. Soc., 114, 3400 (1992); K.-H. Ahn, R. B. Klassen, and S. J. Lippard, Organometallics, 9, 3178 (1990). Zn-catalyzed asymmetric 1,4-addition: J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 55, 4168 (1990).
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