Novel [1,N]-Carbon to Carbon Rearrangement of an Ester Group via Organotitanium Intermediates Wherein the N Varies from 2 to 5. Full Scope and Limitation Leading Predominantly to the Rearrangement

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 7, 1998, Pages 1673-1681

  Yamazaki, Takanori ^a   Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343588787     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1673     Document Type: Article

References (77)

1. For survey on rearrangement reactions, see: a) J. March, "Advanced Organic Chemistry," 4th ed, Wiley, N. Y. (1992), p. 1051; b) M. Hesse, "Ring Enlargement in Organic Chemistry," VCH, Weinheim (1991); c) R. C. Larock, "Comprehensive Organic Transformations," VCH, N. Y. (1989), pp. 627 and 929; d) J. J. Bronson and R. L. Danheiser, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 5, p. 999; e) P. M. Wovkulich, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 843; f) C. J. Roxburgh, Tetrahedron, 47, 10749 (1993); g) H. Stach and M. Hesse, Tetrahedron, 44, 1573 (1988).
2. For survey on rearrangement reactions, see: a) J. March, "Advanced Organic Chemistry," 4th ed, Wiley, N. Y. (1992), p. 1051; b) M. Hesse, "Ring Enlargement in Organic Chemistry," VCH, Weinheim (1991); c) R. C. Larock, "Comprehensive Organic Transformations," VCH, N. Y. (1989), pp. 627 and 929; d) J. J. Bronson and R. L. Danheiser, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 5, p. 999; e) P. M. Wovkulich, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 843; f) C. J. Roxburgh, Tetrahedron, 47, 10749 (1993); g) H. Stach and M. Hesse, Tetrahedron, 44, 1573 (1988).
3. For survey on rearrangement reactions, see: a) J. March, "Advanced Organic Chemistry," 4th ed, Wiley, N. Y. (1992), p. 1051; b) M. Hesse, "Ring Enlargement in Organic Chemistry," VCH, Weinheim (1991); c) R. C. Larock, "Comprehensive Organic Transformations," VCH, N. Y. (1989), pp. 627 and 929; d) J. J. Bronson and R. L. Danheiser, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 5, p. 999; e) P. M. Wovkulich, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 843; f) C. J. Roxburgh, Tetrahedron, 47, 10749 (1993); g) H. Stach and M. Hesse, Tetrahedron, 44, 1573 (1988).
4. For survey on rearrangement reactions, see: a) J. March, "Advanced Organic Chemistry," 4th ed, Wiley, N. Y. (1992), p. 1051; b) M. Hesse, "Ring Enlargement in Organic Chemistry," VCH, Weinheim (1991); c) R. C. Larock, "Comprehensive Organic Transformations," VCH, N. Y. (1989), pp. 627 and 929; d) J. J. Bronson and R. L. Danheiser, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 5, p. 999; e) P. M. Wovkulich, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 843; f) C. J. Roxburgh, Tetrahedron, 47, 10749 (1993); g) H. Stach and M. Hesse, Tetrahedron, 44, 1573 (1988).
5. For survey on rearrangement reactions, see: a) J. March, "Advanced Organic Chemistry," 4th ed, Wiley, N. Y. (1992), p. 1051; b) M. Hesse, "Ring Enlargement in Organic Chemistry," VCH, Weinheim (1991); c) R. C. Larock, "Comprehensive Organic Transformations," VCH, N. Y. (1989), pp. 627 and 929; d) J. J. Bronson and R. L. Danheiser, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 5, p. 999; e) P. M. Wovkulich, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 843; f) C. J. Roxburgh, Tetrahedron, 47, 10749 (1993); g) H. Stach and M. Hesse, Tetrahedron, 44, 1573 (1988).
6. For survey on rearrangement reactions, see: a) J. March, "Advanced Organic Chemistry," 4th ed, Wiley, N. Y. (1992), p. 1051; b) M. Hesse, "Ring Enlargement in Organic Chemistry," VCH, Weinheim (1991); c) R. C. Larock, "Comprehensive Organic Transformations," VCH, N. Y. (1989), pp. 627 and 929; d) J. J. Bronson and R. L. Danheiser, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 5, p. 999; e) P. M. Wovkulich, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 843; f) C. J. Roxburgh, Tetrahedron, 47, 10749 (1993); g) H. Stach and M. Hesse, Tetrahedron, 44, 1573 (1988).
7. For survey on rearrangement reactions, see: a) J. March, "Advanced Organic Chemistry," 4th ed, Wiley, N. Y. (1992), p. 1051; b) M. Hesse, "Ring Enlargement in Organic Chemistry," VCH, Weinheim (1991); c) R. C. Larock, "Comprehensive Organic Transformations," VCH, N. Y. (1989), pp. 627 and 929; d) J. J. Bronson and R. L. Danheiser, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 5, p. 999; e) P. M. Wovkulich, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 843; f) C. J. Roxburgh, Tetrahedron, 47, 10749 (1993); g) H. Stach and M. Hesse, Tetrahedron, 44, 1573 (1988).
8. For the notion "atom economy," see: B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995); B. M. Trost, Science, 254, 1471 (1991).
9. For the notion "atom economy," see: B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995); B. M. Trost, Science, 254, 1471 (1991).
10. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
11. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
12. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
13. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
14. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
15. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
16. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
17. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
18. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
19. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
20. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
21. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
22. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
23. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
24. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
25. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
26. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
27. Ref. 1b, p. 125; C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 62, 560 (1940); S. Hünig and H. Hoch, Chem. Ber., 105, 2197 (1972); P. Caubère, M. S. Mourad, and G. Guillaumet, Tetrahedron, 29, 1851 (1973); P. Caubere, G. Guillaumet, and M. S. Mourad, Tetrahedron, 29, 1857 (1973); P. Caubere and L. Lallotz, J. Org. Chem., 40, 2853 (1975); B. M. Trost and J. E. Vincent, J. Am. Chem. Soc., 102, 5680 (1980); A. Lorenzi-Riatsch, Y. Nakashita, and M. Hesse, Helv. Chim. Acta, 64, 1854 (1981); Y. Nakashita and M. Hesse, Angew. Chem., Int. Ed. Engl., 20, 1021 (1981); Y. Nakashita and M. Hesse, Helv. Chim. Acta, 66, 845 (1983); M. Susse, J. Hájicek, and M. Hesse, Helv. Chim. Acta, 68, 1986 (1985): E. Benkert and M. Hesse, Helv. Chim. Acta, 70, 2166 (1987); M.-C. Carre, B. Jamart-Gregoire, P. Geoffroy, and P. Caubere, Tetrahedron, 44, 127 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1988, 1638; S. Bienz and M. Hesse, Helv. Chim. Acta, 71, 1704 (1988); Z.-F. Xie, H. Suemune, and K. Sakai, Synth. Commun., 19, 987 (1988); M. Mori, N. Isono, N. Kaneta, and M. Shibasaki, J. Org. Chem., 58, 2972 (1993); C.-J. Li, D.-L. Chen, Y.-Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996); J. X. Haberman and C.-J. Li, Tetrahedron Lett., 38, 4735 (1997).
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43. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
44. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
45. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
46. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
47. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
48. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
49. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
50. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
51. A. Kasatkin and F. Sato, Tetrahedron Lett., 36, 6079 (1995); A. Kasatkin, S. Okamoto, and F. Sato, Tetrahedron Lett., 36, 6075 (1995); P. K. Zubaidha, A. Kasatkin, and F. Sato, Chem. Commun., 1996, 197; V. Chaplinski and A. de Meijere, Angew. Chem., Int. Ed. Engl., 35, 413 (1996); A. Kasatkin, K. Kobayashi, S. Okamoto, and F. Sato, Tetrahedron Lett., 37, 1849 (1996); J. Lee, C. H. Kang, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 291 (1996); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 118, 4198 (1996); J. Lee, Y. G. Kim, J. Bae, and J. K. Cha, J. Org. Chem., 61, 4878 (1996); Y. Yoshida, S. Okamoto, and F. Sato, J. Org. Chem., 61, 7826 (1996); J. Lee and J. K. Cha, J. Org. Chem., 62, 1584 (1997); V. Chaplinski, H. Winsel, M. Kordes, and A. de Meijere, Synlett, 1997, 111.
52. K. Suzuki, H. Urabe, and F. Sato, J. Am. Chem. Soc., 118, 8729 (1996); H. Urabe, K. Suzuki, and F. Sato, J. Am. Chem. Soc., 119, 10014 (1997).
53. K. Suzuki, H. Urabe, and F. Sato, J. Am. Chem. Soc., 118, 8729 (1996); H. Urabe, K. Suzuki, and F. Sato, J. Am. Chem. Soc., 119, 10014 (1997).
54. A part of this work was communicated. See: Kasatkin, T. Yamazaki, and F. Sato, Angew. Chem., Int. Ed. Engl., 35, 1966 (1996).
55. 2,2-Disubstituted 1,3-dicarbonyl compounds are susceptible to the 1,2-cleavage with a nucleophile. H. O. House, "Modern Synthetic Reactions," 2nd ed, Benjamin, Menlo Park (1972), p. 517.
56. 4 and Grignard reagents was first reported by Kulinkovich et al. They utilized this complex as a 1,2-bis-anionic species. See: O. G. Kulinkovich, S. V. Sviridov, and D. A. Vasilevski, Synthesis, 1991, 234. See also: A. de Meijere, S. I. Kozhushkov, T. Spaeth, and N. S. Zefirov, J. Org. Chem., 58, 502 (1993); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 117, 9919 (1995); E. J. Corey, S. A. Rao, and M. C. Noe, J. Am. Chem. Soc., 116, 9345 (1994).
57. 4 and Grignard reagents was first reported by Kulinkovich et al. They utilized this complex as a 1,2-bis-anionic species. See: O. G. Kulinkovich, S. V. Sviridov, and D. A. Vasilevski, Synthesis, 1991, 234. See also: A. de Meijere, S. I. Kozhushkov, T. Spaeth, and N. S. Zefirov, J. Org. Chem., 58, 502 (1993); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 117, 9919 (1995); E. J. Corey, S. A. Rao, and M. C. Noe, J. Am. Chem. Soc., 116, 9345 (1994).
58. 4 and Grignard reagents was first reported by Kulinkovich et al. They utilized this complex as a 1,2-bis-anionic species. See: O. G. Kulinkovich, S. V. Sviridov, and D. A. Vasilevski, Synthesis, 1991, 234. See also: A. de Meijere, S. I. Kozhushkov, T. Spaeth, and N. S. Zefirov, J. Org. Chem., 58, 502 (1993); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 117, 9919 (1995); E. J. Corey, S. A. Rao, and M. C. Noe, J. Am. Chem. Soc., 116, 9345 (1994).
59. 4 and Grignard reagents was first reported by Kulinkovich et al. They utilized this complex as a 1,2-bis-anionic species. See: O. G. Kulinkovich, S. V. Sviridov, and D. A. Vasilevski, Synthesis, 1991, 234. See also: A. de Meijere, S. I. Kozhushkov, T. Spaeth, and N. S. Zefirov, J. Org. Chem., 58, 502 (1993); J. Lee, H. Kim, and J. K. Cha, J. Am. Chem. Soc., 117, 9919 (1995); E. J. Corey, S. A. Rao, and M. C. Noe, J. Am. Chem. Soc., 116, 9345 (1994).
60. Similar titanium species having aryloxy groups in place of the alkoxy group is known. G. J. Balaich and I. P. Rothwell, J. Am. Chem. Soc., 115, 1581 (1993); G. J. Balaich and I. P. Rothwell, Tetrahedron, 51, 4463 (1995).
61. Similar titanium species having aryloxy groups in place of the alkoxy group is known. G. J. Balaich and I. P. Rothwell, J. Am. Chem. Soc., 115, 1581 (1993); G. J. Balaich and I. P. Rothwell, Tetrahedron, 51, 4463 (1995).
62. 4 and i-PrMgCl as a divalent titanium reagent, see: a) Ref. 7a;
63. b) K. Harada, H. Urabe, and F. Sato, Tetrahedron Lett., 36, 3203 (1995).
64. J. L. Herrmann, G. R. Kieczykowsky, and R. H. Schlessinger, Tetrahedron Lett., 1973, 2433.
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67. K. Yamashita, H. Urabe, and F. Sato, Tetrahedron Lett., 38, 4619 (1997); Y. Takayanagi, K. Yamashita, Y. Yoshida, and F. Sato, Chem. Commun., 1996, 1725; K. Yamashita and F. Sato, Tetrahedron Lett., 37, 7275 (1996).
68. K. Yamashita, H. Urabe, and F. Sato, Tetrahedron Lett., 38, 4619 (1997); Y. Takayanagi, K. Yamashita, Y. Yoshida, and F. Sato, Chem. Commun., 1996, 1725; K. Yamashita and F. Sato, Tetrahedron Lett., 37, 7275 (1996).
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70. G. R. Newkome and G. R. Baker, Org. Prep. Proced. Int., 18, 117 (1986); G. Cravotto, G. B. Giovenzana, M. Sisti, and G. Palmisano, Tetrahedron, 52, 13007 (1996).
71. For reviews on the reactivity of organotitanium reagents. See: M. T. Reetz, "Organotitanium Reagents in Organic Synthesis," Springer-Verlag, Berlin (1986); C. Ferreri, G. Palumbo, and R. Caputo, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 139; M. T. Reetz, "Organometallics in Synthesis," ed by M. Schlosser, Wiley, Chichester (1994), p. 195.
72. For reviews on the reactivity of organotitanium reagents. See: M. T. Reetz, "Organotitanium Reagents in Organic Synthesis," Springer-Verlag, Berlin (1986); C. Ferreri, G. Palumbo, and R. Caputo, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 139; M. T. Reetz, "Organometallics in Synthesis," ed by M. Schlosser, Wiley, Chichester (1994), p. 195.
73. For reviews on the reactivity of organotitanium reagents. See: M. T. Reetz, "Organotitanium Reagents in Organic Synthesis," Springer-Verlag, Berlin (1986); C. Ferreri, G. Palumbo, and R. Caputo, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 139; M. T. Reetz, "Organometallics in Synthesis," ed by M. Schlosser, Wiley, Chichester (1994), p. 195.
74. H. Urabe and F. Sato, J. Org. Chem., 61, 6756 (1996). Ordinary alkenyltitanium species were reported to react with aldehydes. R. K. Boeckman, Jr., and K. J. O'Connor, Tetrahedron Lett., 30, 3271 (1989); H. Schick, J. Spanig, R. Mahrwald, M. Bohle, T. Reiher, and K. K. Pivnitsky, Tetrahedron, 48, 5579 (1992).
75. H. Urabe and F. Sato, J. Org. Chem., 61, 6756 (1996). Ordinary alkenyltitanium species were reported to react with aldehydes. R. K. Boeckman, Jr., and K. J. O'Connor, Tetrahedron Lett., 30, 3271 (1989); H. Schick, J. Spanig, R. Mahrwald, M. Bohle, T. Reiher, and K. K. Pivnitsky, Tetrahedron, 48, 5579 (1992).
76. H. Urabe and F. Sato, J. Org. Chem., 61, 6756 (1996). Ordinary alkenyltitanium species were reported to react with aldehydes. R. K. Boeckman, Jr., and K. J. O'Connor, Tetrahedron Lett., 30, 3271 (1989); H. Schick, J. Spanig, R. Mahrwald, M. Bohle, T. Reiher, and K. K. Pivnitsky, Tetrahedron, 48, 5579 (1992).
77. C. G. Boojamra, R. H. Crabtree, R. R. Ferguson, and C. A. Muedas, Tetrahedron Lett., 30, 5583 (1989).