Enantioselective Carbon-Carbon Bond Formation via SN2 Displacements of Acyclic Allylic Mesylates

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 645-653

  Marino, Joseph P ^a   Viso, Alma ^a,c   Lee, Jae Don ^a   De La Pradilla, Roberto Fernández ^b   Fernández, Paloma ^b   Rubio, M Belén ^b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001362528     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961292i     Document Type: Article

References (98)

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2. For leading reviews, see: (a) Oare, D. A.; Heathcock, C. H. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1989; Vol. 19, pp 227-407. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Ibid. Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1982; Vol. 13, pp 1-115. (c) Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1-103. (d) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209. (d) Bartlett, P. A. Tetrahedron 1981, 36, 3-72.
3. For leading reviews, see: (a) Oare, D. A.; Heathcock, C. H. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1989; Vol. 19, pp 227-407. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Ibid. Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1982; Vol. 13, pp 1-115. (c) Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1-103. (d) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209. (d) Bartlett, P. A. Tetrahedron 1981, 36, 3-72.
4. For leading reviews, see: (a) Oare, D. A.; Heathcock, C. H. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1989; Vol. 19, pp 227-407. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Ibid. Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1982; Vol. 13, pp 1-115. (c) Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1-103. (d) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209. (d) Bartlett, P. A. Tetrahedron 1981, 36, 3-72.
5. For leading reviews, see: (a) Oare, D. A.; Heathcock, C. H. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1989; Vol. 19, pp 227-407. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Ibid. Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1982; Vol. 13, pp 1-115. (c) Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1-103. (d) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209. (d) Bartlett, P. A. Tetrahedron 1981, 36, 3-72.
6. For leading reviews, see: (a) Oare, D. A.; Heathcock, C. H. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1989; Vol. 19, pp 227-407. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Ibid. Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1982; Vol. 13, pp 1-115. (c) Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1-103. (d) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209. (d) Bartlett, P. A. Tetrahedron 1981, 36, 3-72.
7. For reviews, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. (b) Rayner, C. M. Contemporary Organic Synthesis 1995, 2, 409-440. (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (d) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: New York, 1988. (e) Solladié, G. Synthesis 1981, 185-196.
8. For reviews, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. (b) Rayner, C. M. Contemporary Organic Synthesis 1995, 2, 409-440. (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (d) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: New York, 1988. (e) Solladié, G. Synthesis 1981, 185-196.
9. For reviews, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. (b) Rayner, C. M. Contemporary Organic Synthesis 1995, 2, 409-440. (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (d) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: New York, 1988. (e) Solladié, G. Synthesis 1981, 185-196.
10. For reviews, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. (b) Rayner, C. M. Contemporary Organic Synthesis 1995, 2, 409-440. (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (d) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: New York, 1988. (e) Solladié, G. Synthesis 1981, 185-196.
11. For reviews, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. (b) Rayner, C. M. Contemporary Organic Synthesis 1995, 2, 409-440. (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-968. (d) The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: New York, 1988. (e) Solladié, G. Synthesis 1981, 185-196.
12. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
13. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
14. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
15. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
16. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
17. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
18. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
19. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
20. For leading references, see: (f) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc. Perkin Trans, 1 1994, 15-23. (g) Maezaki, N.; Soejima, M.; Takeda, M.; Sakamoto, A.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1345-1346. (h) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115-118. (i) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (j) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508. (k) Girodier, L. D.; Rouessac, F. P. Tetrahedron: Asymmetry 1994, 5, 1203-1206. (1) Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717-1726. (m) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150. (n) Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
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32. For the early report on α-metalation of vinyl sulfoxides, see: (a) Posner, G. H.; Tang, P. W.; Mallamo, J. P. Tetrahedron Lett. 1978, 3995-3998. (b) Okamura, H.; Mitsuhira, Y.; Miura, M.; Takei, H. Chem. Lett. 1978, 517-520.
33. For the early report on α-metalation of vinyl sulfoxides, see: (a) Posner, G. H.; Tang, P. W.; Mallamo, J. P. Tetrahedron Lett. 1978, 3995-3998. (b) Okamura, H.; Mitsuhira, Y.; Miura, M.; Takei, H. Chem. Lett. 1978, 517-520.
34. For other related reports, see: (c) Fawcett, J.; House, S.; Jenkins, P. R.; Lawrence, N. J.; Russell, D. R. J. Chem. Soc., Perkin Trans. 1 1993, 67-73. (d) Cheng, H.-C.; Yan, T.-H. Tetrahedron Lett, 1990, 31, 673-676. (e) House, S.; Jenkins, P. R.; Fawcett, J.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1987, 1844-1845. (f) Holton, R. A.; Kim, H. B. Tetrahedron Lett. 1986, 27, 2191-2194. (g) Posner, G. H.; Kogan, T. P.; Haines, S. R.; Frye, L. L. Tetrahedron Lett. 1984, 25, 2627-2630.
35. For other related reports, see: (c) Fawcett, J.; House, S.; Jenkins, P. R.; Lawrence, N. J.; Russell, D. R. J. Chem. Soc., Perkin Trans. 1 1993, 67-73. (d) Cheng, H.-C.; Yan, T.-H. Tetrahedron Lett, 1990, 31, 673-676. (e) House, S.; Jenkins, P. R.; Fawcett, J.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1987, 1844-1845. (f) Holton, R. A.; Kim, H. B. Tetrahedron Lett. 1986, 27, 2191-2194. (g) Posner, G. H.; Kogan, T. P.; Haines, S. R.; Frye, L. L. Tetrahedron Lett. 1984, 25, 2627-2630.
36. For other related reports, see: (c) Fawcett, J.; House, S.; Jenkins, P. R.; Lawrence, N. J.; Russell, D. R. J. Chem. Soc., Perkin Trans. 1 1993, 67-73. (d) Cheng, H.-C.; Yan, T.-H. Tetrahedron Lett, 1990, 31, 673-676. (e) House, S.; Jenkins, P. R.; Fawcett, J.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1987, 1844-1845. (f) Holton, R. A.; Kim, H. B. Tetrahedron Lett. 1986, 27, 2191-2194. (g) Posner, G. H.; Kogan, T. P.; Haines, S. R.; Frye, L. L. Tetrahedron Lett. 1984, 25, 2627-2630.
37. For other related reports, see: (c) Fawcett, J.; House, S.; Jenkins, P. R.; Lawrence, N. J.; Russell, D. R. J. Chem. Soc., Perkin Trans. 1 1993, 67-73. (d) Cheng, H.-C.; Yan, T.-H. Tetrahedron Lett, 1990, 31, 673-676. (e) House, S.; Jenkins, P. R.; Fawcett, J.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1987, 1844-1845. (f) Holton, R. A.; Kim, H. B. Tetrahedron Lett. 1986, 27, 2191-2194. (g) Posner, G. H.; Kogan, T. P.; Haines, S. R.; Frye, L. L. Tetrahedron Lett. 1984, 25, 2627-2630.
38. For other related reports, see: (c) Fawcett, J.; House, S.; Jenkins, P. R.; Lawrence, N. J.; Russell, D. R. J. Chem. Soc., Perkin Trans. 1 1993, 67-73. (d) Cheng, H.-C.; Yan, T.-H. Tetrahedron Lett, 1990, 31, 673-676. (e) House, S.; Jenkins, P. R.; Fawcett, J.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1987, 1844-1845. (f) Holton, R. A.; Kim, H. B. Tetrahedron Lett. 1986, 27, 2191-2194. (g) Posner, G. H.; Kogan, T. P.; Haines, S. R.; Frye, L. L. Tetrahedron Lett. 1984, 25, 2627-2630.
39. N2′ reactions, see: (a) Marshall, J. A. Chem. Rev. 1989, 89, 1503-1511. (b) Magid, R. M. Tetrahedron 1980, 36, 1901-1930.
40. N2′ reactions, see: (a) Marshall, J. A. Chem. Rev. 1989, 89, 1503-1511. (b) Magid, R. M. Tetrahedron 1980, 36, 1901-1930.
41. For reviews on organocopper chemistry, see: (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188. (d) Wipf, P. Synthesis 1993, 537-557. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631. (f) Kozlowski, J. A.: Organocuprates in the Conjugate Addition Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 169-198. (g) Lipshutz, B. H. Synlett 1990, 119-128. (h) Lipshutz, B. H. Synthesis 1987, 325-341. (i) Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959, and references cited therein.
42. For reviews on organocopper chemistry, see: (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188. (d) Wipf, P. Synthesis 1993, 537-557. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631. (f) Kozlowski, J. A.: Organocuprates in the Conjugate Addition Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 169-198. (g) Lipshutz, B. H. Synlett 1990, 119-128. (h) Lipshutz, B. H. Synthesis 1987, 325-341. (i) Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959, and references cited therein.
43. For reviews on organocopper chemistry, see: (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188. (d) Wipf, P. Synthesis 1993, 537-557. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631. (f) Kozlowski, J. A.: Organocuprates in the Conjugate Addition Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 169-198. (g) Lipshutz, B. H. Synlett 1990, 119-128. (h) Lipshutz, B. H. Synthesis 1987, 325-341. (i) Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959, and references cited therein.
44. For reviews on organocopper chemistry, see: (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188. (d) Wipf, P. Synthesis 1993, 537-557. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631. (f) Kozlowski, J. A.: Organocuprates in the Conjugate Addition Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 169-198. (g) Lipshutz, B. H. Synlett 1990, 119-128. (h) Lipshutz, B. H. Synthesis 1987, 325-341. (i) Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959, and references cited therein.
45. For reviews on organocopper chemistry, see: (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188. (d) Wipf, P. Synthesis 1993, 537-557. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631. (f) Kozlowski, J. A.: Organocuprates in the Conjugate Addition Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 169-198. (g) Lipshutz, B. H. Synlett 1990, 119-128. (h) Lipshutz, B. H. Synthesis 1987, 325-341. (i) Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959, and references cited therein.
46. For reviews on organocopper chemistry, see: (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188. (d) Wipf, P. Synthesis 1993, 537-557. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631. (f) Kozlowski, J. A.: Organocuprates in the Conjugate Addition Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 169-198. (g) Lipshutz, B. H. Synlett 1990, 119-128. (h) Lipshutz, B. H. Synthesis 1987, 325-341. (i) Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959, and references cited therein.
47. For reviews on organocopper chemistry, see: (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188. (d) Wipf, P. Synthesis 1993, 537-557. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631. (f) Kozlowski, J. A.: Organocuprates in the Conjugate Addition Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 169-198. (g) Lipshutz, B. H. Synlett 1990, 119-128. (h) Lipshutz, B. H. Synthesis 1987, 325-341. (i) Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959, and references cited therein.
48. For leading references on copper-mediated cross-coupling reactions with allylic derivatives, see: (j) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453-2466. (k) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1993, 59, 4126-4130. (1) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129. (m) Ibuka, T.; Suzuki, K.; Habashita, H.; Otaka, A.; Tamamura, H.; Mimura, N.; Miwa, Y.; Taga, T.; Fujii, N. J. Chem. Soc., Chem. Commun. 1994, 2151-2152. (n) Girard, C.; Mandville, G.; Bloch, R. Tetrahedron: Asymmetry 1993, 4, 613-616. (o) Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94. (p) Valverde, S.; Bernabé, M.; Gómez, A. M.; Puebla, P. J. Org. Chem. 1992, 57, 4546-4550.
49. For leading references on copper-mediated cross-coupling reactions with allylic derivatives, see: (j) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453-2466. (k) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1993, 59, 4126-4130. (1) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129. (m) Ibuka, T.; Suzuki, K.; Habashita, H.; Otaka, A.; Tamamura, H.; Mimura, N.; Miwa, Y.; Taga, T.; Fujii, N. J. Chem. Soc., Chem. Commun. 1994, 2151-2152. (n) Girard, C.; Mandville, G.; Bloch, R. Tetrahedron: Asymmetry 1993, 4, 613-616. (o) Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94. (p) Valverde, S.; Bernabé, M.; Gómez, A. M.; Puebla, P. J. Org. Chem. 1992, 57, 4546-4550.
50. For leading references on copper-mediated cross-coupling reactions with allylic derivatives, see: (j) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453-2466. (k) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1993, 59, 4126-4130. (1) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129. (m) Ibuka, T.; Suzuki, K.; Habashita, H.; Otaka, A.; Tamamura, H.; Mimura, N.; Miwa, Y.; Taga, T.; Fujii, N. J. Chem. Soc., Chem. Commun. 1994, 2151-2152. (n) Girard, C.; Mandville, G.; Bloch, R. Tetrahedron: Asymmetry 1993, 4, 613-616. (o) Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94. (p) Valverde, S.; Bernabé, M.; Gómez, A. M.; Puebla, P. J. Org. Chem. 1992, 57, 4546-4550.
51. For leading references on copper-mediated cross-coupling reactions with allylic derivatives, see: (j) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453-2466. (k) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1993, 59, 4126-4130. (1) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129. (m) Ibuka, T.; Suzuki, K.; Habashita, H.; Otaka, A.; Tamamura, H.; Mimura, N.; Miwa, Y.; Taga, T.; Fujii, N. J. Chem. Soc., Chem. Commun. 1994, 2151-2152. (n) Girard, C.; Mandville, G.; Bloch, R. Tetrahedron: Asymmetry 1993, 4, 613-616. (o) Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94. (p) Valverde, S.; Bernabé, M.; Gómez, A. M.; Puebla, P. J. Org. Chem. 1992, 57, 4546-4550.
52. For leading references on copper-mediated cross-coupling reactions with allylic derivatives, see: (j) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453-2466. (k) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1993, 59, 4126-4130. (1) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129. (m) Ibuka, T.; Suzuki, K.; Habashita, H.; Otaka, A.; Tamamura, H.; Mimura, N.; Miwa, Y.; Taga, T.; Fujii, N. J. Chem. Soc., Chem. Commun. 1994, 2151-2152. (n) Girard, C.; Mandville, G.; Bloch, R. Tetrahedron: Asymmetry 1993, 4, 613-616. (o) Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94. (p) Valverde, S.; Bernabé, M.; Gómez, A. M.; Puebla, P. J. Org. Chem. 1992, 57, 4546-4550.
53. For leading references on copper-mediated cross-coupling reactions with allylic derivatives, see: (j) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453-2466. (k) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1993, 59, 4126-4130. (1) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129. (m) Ibuka, T.; Suzuki, K.; Habashita, H.; Otaka, A.; Tamamura, H.; Mimura, N.; Miwa, Y.; Taga, T.; Fujii, N. J. Chem. Soc., Chem. Commun. 1994, 2151-2152. (n) Girard, C.; Mandville, G.; Bloch, R. Tetrahedron: Asymmetry 1993, 4, 613-616. (o) Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94. (p) Valverde, S.; Bernabé, M.; Gómez, A. M.; Puebla, P. J. Org. Chem. 1992, 57, 4546-4550.
54. For leading references on copper-mediated cross-coupling reactions with allylic derivatives, see: (j) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453-2466. (k) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1993, 59, 4126-4130. (1) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129. (m) Ibuka, T.; Suzuki, K.; Habashita, H.; Otaka, A.; Tamamura, H.; Mimura, N.; Miwa, Y.; Taga, T.; Fujii, N. J. Chem. Soc., Chem. Commun. 1994, 2151-2152. (n) Girard, C.; Mandville, G.; Bloch, R. Tetrahedron: Asymmetry 1993, 4, 613-616. (o) Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetrahedron Lett. 1993, 34, 91-94. (p) Valverde, S.; Bernabé, M.; Gómez, A. M.; Puebla, P. J. Org. Chem. 1992, 57, 4546-4550.
55. Low stereoselectivities have been reported for these processes. See: (a) Posner, G. H.; Mallamo, P.; Miura, K.; Hulce, M. Pure Appl. Chem. 1981, 54, 2307-2314.
56. For one example in which a high diastereoselectivity was found, see: (b) Solladié, G.; Moine, G. J. Am. Chem. Soc. 1984, 106, 6097-6098.
57. Trapping of the vinyl anion with propionyl chloride or ethyl propionate, more direct routes to 6, failed in our hands.
58. 3; 9-BBN.
59. (a) Grynkiewicz, G.; Burzynska, H. Tetrahedron 1976, 32, 2109-2111.
60. (b) Hughes, D. L., Org. React. 1992, 42, 335-669.
61. Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 2318-2325.
62. Amri, H.; Rambaud, M.; Villieras, J. Tetrahedron 1990, 46, 3535-3546.
63. For pertinent references on coupling of cuprates with allylic carboxylates, see: Underiner, T. L.; Paisley, S. D.; Schmitter, J.; Lesheski, L.; Goering, H. L. J. Org. Chem. 1989, 54, 2369-2374 and references cited therein.
64. (a) Fujii. N.; Nakai, K.; Habashita, H.; Yoshizawa, H.; Ibuka, T.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 4227-4230.
65. (b) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207-1214.
66. (c) Ibuka, T.; Yoshizawa, H.; Habashita, H.; Fujii, N.; Chounan, Y.; Tanaka, M.; Yamamoto, Y. Tetrahedron Lett. 1992, 33, 3783-3786.
67. (d) Ibuka, T.; Yamamoto, Y. Synlett 1992, 769-777 and references cited therein.
68. (e) Burke, S. D.; Piscopio, A. D.; Kort, M. E. Tetrahedron Lett. 1991, 32, 855-856.
69. 3, 300 MHz) δ 1.77 (d, 3 H, J = 5.1 Hz), 2.38 (s, 3 H), 6.06 (dq, 1 H, J = 16.2, 5.5 Hz), 6.20 (d, 1 H, J = 16.5 Hz), 7.26-7.60 (m, 10 H). For other reports on enantiomerically pure 2-sulfmyl dienes, see: (a) Paley, R. S.; Weers, H. L.; Fernández, P.; Fernández de la Pradilla, R.; Castro, S. Tetrahedron Lett. 1995, 36, 3605-3608. (b) Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron: Asymmetry 1993, 4, 1667-1676. (c) Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron Lett. 1992, 33, 2347-2348. (d) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jafari, S. M. A.; Jones, D. N. Tetrahedron: Asymmetry 1992, 3, 701-704. For reports on the highly stereoselective Diels-Alder reactivity of these dienes, see: (e) Gosselin, P.; Bonfand, P.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781-784. (f) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jones, D. N. Ibid. 1994, 5, 805-808.
70. 3, 300 MHz) δ 1.77 (d, 3 H, J = 5.1 Hz), 2.38 (s, 3 H), 6.06 (dq, 1 H, J = 16.2, 5.5 Hz), 6.20 (d, 1 H, J = 16.5 Hz), 7.26-7.60 (m, 10 H). For other reports on enantiomerically pure 2-sulfmyl dienes, see: (a) Paley, R. S.; Weers, H. L.; Fernández, P.; Fernández de la Pradilla, R.; Castro, S. Tetrahedron Lett. 1995, 36, 3605-3608. (b) Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron: Asymmetry 1993, 4, 1667-1676. (c) Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron Lett. 1992, 33, 2347-2348. (d) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jafari, S. M. A.; Jones, D. N. Tetrahedron: Asymmetry 1992, 3, 701-704. For reports on the highly stereoselective Diels-Alder reactivity of these dienes, see: (e) Gosselin, P.; Bonfand, P.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781-784. (f) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jones, D. N. Ibid. 1994, 5, 805-808.
71. 3, 300 MHz) δ 1.77 (d, 3 H, J = 5.1 Hz), 2.38 (s, 3 H), 6.06 (dq, 1 H, J = 16.2, 5.5 Hz), 6.20 (d, 1 H, J = 16.5 Hz), 7.26-7.60 (m, 10 H). For other reports on enantiomerically pure 2-sulfmyl dienes, see: (a) Paley, R. S.; Weers, H. L.; Fernández, P.; Fernández de la Pradilla, R.; Castro, S. Tetrahedron Lett. 1995, 36, 3605-3608. (b) Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron: Asymmetry 1993, 4, 1667-1676. (c) Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron Lett. 1992, 33, 2347-2348. (d) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jafari, S. M. A.; Jones, D. N. Tetrahedron: Asymmetry 1992, 3, 701-704. For reports on the highly stereoselective Diels-Alder reactivity of these dienes, see: (e) Gosselin, P.; Bonfand, P.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781-784. (f) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jones, D. N. Ibid. 1994, 5, 805-808.
72. 3, 300 MHz) δ 1.77 (d, 3 H, J = 5.1 Hz), 2.38 (s, 3 H), 6.06 (dq, 1 H, J = 16.2, 5.5 Hz), 6.20 (d, 1 H, J = 16.5 Hz), 7.26-7.60 (m, 10 H). For other reports on enantiomerically pure 2-sulfmyl dienes, see: (a) Paley, R. S.; Weers, H. L.; Fernández, P.; Fernández de la Pradilla, R.; Castro, S. Tetrahedron Lett. 1995, 36, 3605-3608. (b) Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron: Asymmetry 1993, 4, 1667-1676. (c) Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron Lett. 1992, 33, 2347-2348. (d) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jafari, S. M. A.; Jones, D. N. Tetrahedron: Asymmetry 1992, 3, 701-704. For reports on the highly stereoselective Diels-Alder reactivity of these dienes, see: (e) Gosselin, P.; Bonfand, P.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781-784. (f) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jones, D. N. Ibid. 1994, 5, 805-808.
73. For reports on the highly stereoselective Diels-Alder reactivity of these dienes, see: (e) Gosselin, P.; Bonfand, P.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781-784.
74. For reports on the highly stereoselective Diels-Alder reactivity of these dienes, see: (e) Gosselin, P.; Bonfand, P.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781-784. (f) Aversa, M. C.; Bonaccorsi, P.; Gianneto, P.; Jones, D. N. Ibid. 1994, 5, 805-808.
75. Under these conditions, the major product found was assigned as PhCH=C=CHEt. For a discussion of these allene producing experiments, see: Fernández de la Pradilla, R.; Rubio, M. B.; Marino, J. P.; Viso, A. Tetrahedron Lett. 1992, 33, 4985-4988.
76. The behavior for the enantiomeric series of phenyl-substituted sulfinyl alcohols, ent-2a and ent-3a (prepared in a standard fashion from commercially available (+)-menthyl (Rs)-p-toluenesulfmate) was examined, giving rise to the expected displacement products ent-9a and ent-11a with good yields and stereoselectivities. These products were fully characterized by spectroscopic techniques, and their data was found to be identical to their corresponding enantiomers with the exception of the sign of their optical rotation. Chemical equation presented.
77. Enantiopure alkenes are frequently found in nature. The structure of some pheromones is an example, see: The Synthesis of Insect Pheromones. In The Total Synthesis of Natural Products; Mori, K., ApSimon, J., Eds.; John Wiley & Sons: New York, 1992; Vol. 9.
78. Park, G.; Okamura, W. H. Synth. Commun. 1991, 21, 1047-1054.
79. N2′ displacements involving organocopper reagents, see ref 15b and references cited therein. See also ref 5d.
80. Mesylates 5c and 4c produce "crossover" products only in a formal sense due to the exchange of the ligand on copper and the R group on the mesylate.
81. Auvray, P.; Knochel, P.; Normant, J. F. Tetrahedron 1988, 44, 6095-6106.
82. N2′ processes on cyclic vinyl sulfones, see: (a) Arjona, O.; de Dios, A.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906-3916. (b) Braish, T.; Saddler, J. C.; Fuchs, P. L. J. Org. Chem. 1988, 53, 3647-3658. (c) Saddler, J. C.; Fuchs, P. L. J. Am. Chem. Soc. 1981, 103, 2112-2114.
83. N2′ processes on cyclic vinyl sulfones, see: (a) Arjona, O.; de Dios, A.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906-3916. (b) Braish, T.; Saddler, J. C.; Fuchs, P. L. J. Org. Chem. 1988, 53, 3647-3658. (c) Saddler, J. C.; Fuchs, P. L. J. Am. Chem. Soc. 1981, 103, 2112-2114.
84. N2′ processes on cyclic vinyl sulfones, see: (a) Arjona, O.; de Dios, A.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906-3916. (b) Braish, T.; Saddler, J. C.; Fuchs, P. L. J. Org. Chem. 1988, 53, 3647-3658. (c) Saddler, J. C.; Fuchs, P. L. J. Am. Chem. Soc. 1981, 103, 2112-2114.
85. Vinyl sulfones are versatile synthetic intermediates. For reviews, see: (a) Simpkins, N. S. Sulphones in Organic Synthesis; Tetrahedron Organic Chemistry Series, Vol. 10; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1993. (b) Cossu, S.; De Lucchi, O.; Fabbri, D. Org. Prep. Proced. Int. 1991, 23, 571-592. (c) Simpkins, N. S. Tetrahedron 1990, 46, 6951-6984. (d) See ref 3b. (e) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755-6794. (f) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903-917.
86. Vinyl sulfones are versatile synthetic intermediates. For reviews, see: (a) Simpkins, N. S. Sulphones in Organic Synthesis; Tetrahedron Organic Chemistry Series, Vol. 10; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1993. (b) Cossu, S.; De Lucchi, O.; Fabbri, D. Org. Prep. Proced. Int. 1991, 23, 571-592. (c) Simpkins, N. S. Tetrahedron 1990, 46, 6951-6984. (d) See ref 3b. (e) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755-6794. (f) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903-917.
87. Vinyl sulfones are versatile synthetic intermediates. For reviews, see: (a) Simpkins, N. S. Sulphones in Organic Synthesis; Tetrahedron Organic Chemistry Series, Vol. 10; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1993. (b) Cossu, S.; De Lucchi, O.; Fabbri, D. Org. Prep. Proced. Int. 1991, 23, 571-592. (c) Simpkins, N. S. Tetrahedron 1990, 46, 6951-6984. (d) See ref 3b. (e) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755-6794. (f) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903-917.
88. Vinyl sulfones are versatile synthetic intermediates. For reviews, see: (a) Simpkins, N. S. Sulphones in Organic Synthesis; Tetrahedron Organic Chemistry Series, Vol. 10; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1993. (b) Cossu, S.; De Lucchi, O.; Fabbri, D. Org. Prep. Proced. Int. 1991, 23, 571-592. (c) Simpkins, N. S. Tetrahedron 1990, 46, 6951-6984. (d) See ref 3b. (e) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755-6794. (f) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903-917.
89. Vinyl sulfones are versatile synthetic intermediates. For reviews, see: (a) Simpkins, N. S. Sulphones in Organic Synthesis; Tetrahedron Organic Chemistry Series, Vol. 10; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1993. (b) Cossu, S.; De Lucchi, O.; Fabbri, D. Org. Prep. Proced. Int. 1991, 23, 571-592. (c) Simpkins, N. S. Tetrahedron 1990, 46, 6951-6984. (d) See ref 3b. (e) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755-6794. (f) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903-917.
90. Vinyl sulfones are versatile synthetic intermediates. For reviews, see: (a) Simpkins, N. S. Sulphones in Organic Synthesis; Tetrahedron Organic Chemistry Series, Vol. 10; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1993. (b) Cossu, S.; De Lucchi, O.; Fabbri, D. Org. Prep. Proced. Int. 1991, 23, 571-592. (c) Simpkins, N. S. Tetrahedron 1990, 46, 6951-6984. (d) See ref 3b. (e) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755-6794. (f) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903-917.
91. For leading references, see: (g) Isobe, M.; Jiang, Y. Tetrahedron Lett. 1995, 36, 567-570. (h) Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. (i) Carretero, J. C.; Diaz, N.; Rojo, J.; Tetrahedron Lett. 1994, 35, 6917-6920. (J) Padwa, A.; Filipkowski, M. A.; Meske, M.; Murphree, S. S.; Watterson, S. H.; Ni, Z. J. Org. Chem. 1994, 59, 588-596. (k) Li, C.; Fuchs, P. L. Synlett 1994, 629-630.
92. For leading references, see: (g) Isobe, M.; Jiang, Y. Tetrahedron Lett. 1995, 36, 567-570. (h) Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. (i) Carretero, J. C.; Diaz, N.; Rojo, J.; Tetrahedron Lett. 1994, 35, 6917-6920. (J) Padwa, A.; Filipkowski, M. A.; Meske, M.; Murphree, S. S.; Watterson, S. H.; Ni, Z. J. Org. Chem. 1994, 59, 588-596. (k) Li, C.; Fuchs, P. L. Synlett 1994, 629-630.
93. For leading references, see: (g) Isobe, M.; Jiang, Y. Tetrahedron Lett. 1995, 36, 567-570. (h) Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. (i) Carretero, J. C.; Diaz, N.; Rojo, J.; Tetrahedron Lett. 1994, 35, 6917-6920. (J) Padwa, A.; Filipkowski, M. A.; Meske, M.; Murphree, S. S.; Watterson, S. H.; Ni, Z. J. Org. Chem. 1994, 59, 588-596. (k) Li, C.; Fuchs, P. L. Synlett 1994, 629-630.
94. For leading references, see: (g) Isobe, M.; Jiang, Y. Tetrahedron Lett. 1995, 36, 567-570. (h) Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949-1951. (i) Carretero, J. C.; Diaz, N.; Rojo, J.; Tetrahedron Lett. 1994, 35, 6917-6920. (J) Padwa, A.; Filipkowski, M. A.; Meske, M.; Murphree, S. S.; Watterson, S. H.; Ni, Z. J. Org. Chem. 1994, 59, 588-596. (k) Li, C.; Fuchs, P. L. Synlett 1994, 629-630.
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