Sulfonyl-stabilized allylic norbornenyl and norbornyl carbanions: Structure and stereoselectivity of reaction with electrophiles

European Journal of Organic Chemistry

Volumn , Issue 7, 1999, Pages 1627-1651

  Gais, Hans Joachim ^a   Van Gumpel, Markus ^a   Raabe, Gerhard ^a   Müller, Jürgen ^b   Braun, Siegmar ^c   Lindner, Hans Jörg ^c   Rohs, Susanne ^a   Runsink, Jan ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITY OF BASEL   (Switzerland)

^c DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Ab initio calculations; Aggregation; Lithioallyl sulfones; NMR spectroscopy; Norbornenyl carbanions; Norbornyl carbanions; Stereoselective alkylation; X ray crystal structures

Indexed keywords

NORBORNANE DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0032798729     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199907)1999:7<1627::AID-EJOC1627>3.0.CO;2-9     Document Type: Article

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40. For reviews, see: J.-F. Biellman, J.-B. Ducep, Org. React. 1982, 27, 1-344; S. Oae, Y. Uchida in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling, ), Wiley, New York, 1988, pp. 583-664; K. Ogura in Comprehensive Organic Synthesis (Ed.: S. L. Schreiber), Pergamon Press, Oxford, 1991, vol. 1, pp. 505-539; A. Krief in Comprehensive Organic Synthesis (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, pp. 85-191; Y. Yamamoto in Comprehensive Organic Synthesis (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, vol. 3, pp. 55-79; N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press: Oxford, 1993; M. Braun in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 1713-1735; S. Pyne in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 2068-2086.
41. For reviews, see: J.-F. Biellman, J.-B. Ducep, Org. React. 1982, 27, 1-344; S. Oae, Y. Uchida in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling, ), Wiley, New York, 1988, pp. 583-664; K. Ogura in Comprehensive Organic Synthesis (Ed.: S. L. Schreiber), Pergamon Press, Oxford, 1991, vol. 1, pp. 505-539; A. Krief in Comprehensive Organic Synthesis (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, pp. 85-191; Y. Yamamoto in Comprehensive Organic Synthesis (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, vol. 3, pp. 55-79; N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press: Oxford, 1993; M. Braun in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 1713-1735; S. Pyne in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 2068-2086.
42. For reviews, see: J.-F. Biellman, J.-B. Ducep, Org. React. 1982, 27, 1-344; S. Oae, Y. Uchida in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling, ), Wiley, New York, 1988, pp. 583-664; K. Ogura in Comprehensive Organic Synthesis (Ed.: S. L. Schreiber), Pergamon Press, Oxford, 1991, vol. 1, pp. 505-539; A. Krief in Comprehensive Organic Synthesis (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, pp. 85-191; Y. Yamamoto in Comprehensive Organic Synthesis (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, vol. 3, pp. 55-79; N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press: Oxford, 1993; M. Braun in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 1713-1735; S. Pyne in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 2068-2086.
43. For reviews, see: J.-F. Biellman, J.-B. Ducep, Org. React. 1982, 27, 1-344; S. Oae, Y. Uchida in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling, ), Wiley, New York, 1988, pp. 583-664; K. Ogura in Comprehensive Organic Synthesis (Ed.: S. L. Schreiber), Pergamon Press, Oxford, 1991, vol. 1, pp. 505-539; A. Krief in Comprehensive Organic Synthesis (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, pp. 85-191; Y. Yamamoto in Comprehensive Organic Synthesis (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, vol. 3, pp. 55-79; N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press: Oxford, 1993; M. Braun in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 1713-1735; S. Pyne in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 2068-2086.
44. For reviews, see: J.-F. Biellman, J.-B. Ducep, Org. React. 1982, 27, 1-344; S. Oae, Y. Uchida in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling, ), Wiley, New York, 1988, pp. 583-664; K. Ogura in Comprehensive Organic Synthesis (Ed.: S. L. Schreiber), Pergamon Press, Oxford, 1991, vol. 1, pp. 505-539; A. Krief in Comprehensive Organic Synthesis (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, pp. 85-191; Y. Yamamoto in Comprehensive Organic Synthesis (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, vol. 3, pp. 55-79; N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press: Oxford, 1993; M. Braun in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 1713-1735; S. Pyne in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 2068-2086.
45. For reviews, see: J.-F. Biellman, J.-B. Ducep, Org. React. 1982, 27, 1-344; S. Oae, Y. Uchida in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling, ), Wiley, New York, 1988, pp. 583-664; K. Ogura in Comprehensive Organic Synthesis (Ed.: S. L. Schreiber), Pergamon Press, Oxford, 1991, vol. 1, pp. 505-539; A. Krief in Comprehensive Organic Synthesis (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, pp. 85-191; Y. Yamamoto in Comprehensive Organic Synthesis (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, vol. 3, pp. 55-79; N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press: Oxford, 1993; M. Braun in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 1713-1735; S. Pyne in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 2068-2086.
46. For reviews, see: J.-F. Biellman, J.-B. Ducep, Org. React. 1982, 27, 1-344; S. Oae, Y. Uchida in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling, ), Wiley, New York, 1988, pp. 583-664; K. Ogura in Comprehensive Organic Synthesis (Ed.: S. L. Schreiber), Pergamon Press, Oxford, 1991, vol. 1, pp. 505-539; A. Krief in Comprehensive Organic Synthesis (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, pp. 85-191; Y. Yamamoto in Comprehensive Organic Synthesis (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, vol. 3, pp. 55-79; N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press: Oxford, 1993; M. Braun in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 1713-1735; S. Pyne in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 2068-2086.
47. For reviews, see: J.-F. Biellman, J.-B. Ducep, Org. React. 1982, 27, 1-344; S. Oae, Y. Uchida in The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling, ), Wiley, New York, 1988, pp. 583-664; K. Ogura in Comprehensive Organic Synthesis (Ed.: S. L. Schreiber), Pergamon Press, Oxford, 1991, vol. 1, pp. 505-539; A. Krief in Comprehensive Organic Synthesis (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, pp. 85-191; Y. Yamamoto in Comprehensive Organic Synthesis (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, vol. 3, pp. 55-79; N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press: Oxford, 1993; M. Braun in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 1713-1735; S. Pyne in Stereoselective Synthesis (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, vol. E21b, pp. 2068-2086.
48. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
49. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
50. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
51. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
52. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
53. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
54. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
55. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
56. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
57. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
58. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
59. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
60. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
61. For selected illustrative examples, see: M. Julia, A. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411-1411; M. Julia, D. Arnold, Bull. Soc. Chim. Fr. 1973, 743-746; B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436; B. M. Trost, N. R. Schmuff, M. J. Miller, J. Am. Chem. Soc. 1980, 102, 5979-5981; S. E. Denmark, M. A. Harmata, J. Am. Chem. Soc. 1982, 104, 4972-4974; T. Mandai, T. Yanagi, K. Araki, Y. Morisaki, M. Kawada, J. Otera, J. Am. Chem. Soc. 1984, 106, 3670-3672; B. M. Trost, M. Reza Ghadiri, J. Am. Chem. Soc. 1984, 106, 7260-7261; J. A. Marshall, R. C. Andrews, J. Org. Chem. 1985, 50, 1602-1606; S. D. A. Street, C. Yeates, P. Kocienski, S. F. Campbell, J. Chem. Soc., Chem. Commun. 1985, 1386-1388; T. Cuvigny, C. Herve du Penhoat, M. Julia, Tetrahedron 1986, 42, 5329-5336; B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218; H.-J. Gais, W. A. Ball, J. Bund, Tetrahedron Lett. 1988, 29, 781-784; A. Padwa, S. H. Watterson, Z. Ni, J. Org. Chem. 1994, 59, 3256-3258; Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 117, 3022-3028.
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68. In all experiments with sulfones 5 and 6 described in this work the racemates were used.
69. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-102801 and CCDC-102802. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [Fax: (internat.) + 44-1223/336-033, E-mail: deposit@ccdc.cam.ac.uk).
70. Because of severe disorder problems the crystal structure of exo-6 could not be solved.
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85. G. Boche, M. Marsch, K. Harms, G. M. Sheldrick, Angew. Chem. 1985, 97, 577-578; Angew. Chem. Int. Ed. Engl. 1985, 24, 573-574; W. Hollstein, K. Harms, M. Marsch, G. Boche, Angew. Chem. 1987, 99, 1279-1280; Angew. Chem. Int. Ed. Engl. 1987, 26, 1287-1288; W. Hollstein, K. Harms, M. Marsch, G. Boche, Angew. Chem. 1988, 100, 868-869; Angew Chem. Int. Ed. Engl. 1988, 27, 846-847;
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