Highly diastereoselective intramolecular allylation reactions of mixed silyl-substituted acetals

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2441-2453

  Linderman, Russell J ^a   Chen, Kangyi ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007572683     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9517048     Document Type: Article

References (54)

1. (a) Fleming, I. Chem. Soc. Rev. 1981, 10, 83.
2. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
3. (c) Majetich, G. In Organic Synthesis. Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, p 173.
4. (d) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57.
5. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
6. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
7. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
8. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
9. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
10. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
11. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
12. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
13. E′ addition from a bis-silyl-substituted species, see: Wetter, H.; Scherer, P ; Schweizer, W B. Helv. Chim. Acta 1979, 1985. (i) Mayr, H.; Gorath, G. J. Am Chem. Soc. 1995, 117, 7862.
14. (a) Reetz, M. T.; Jung, A ; Bolm, C. Tetrahedron 1988, 44, 3889.
15. (b) Uyeo, S.; Itani, H. Tetrahedron Lett. 1991, 32, 2143.
16. (a) Linderman, R. J.; Anklekar, T. V. J. Org. Chem. 1992, 57, 5078.
17. (b) Linderman, R. J.; Viviani, F. G.; Kwochka, W. R. Tetrahedron Lett. 1992, 33, 3571.
18. Linderman, R. J ; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 1392.
19. Dihalodialkylsilanes have been employed in the preparation of a wide variety of bisfunctionalized silane derivatives. The "temporary silicon connection" methodology of Stork provides an example of this approach. See, for example: (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; Kim, G. J. Am. Chem, 1992, 114, 1087. (c) Matsumoto, Y.; Ohno, A.; Hayashi, T. Organametallics 1993, 12, 4051.
20. Dihalodialkylsilanes have been employed in the preparation of a wide variety of bisfunctionalized silane derivatives. The "temporary silicon connection" methodology of Stork provides an example of this approach. See, for example: (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; Kim, G. J. Am. Chem, 1992, 114, 1087. (c) Matsumoto, Y.; Ohno, A.; Hayashi, T. Organametallics 1993, 12, 4051.
21. Dihalodialkylsilanes have been employed in the preparation of a wide variety of bisfunctionalized silane derivatives. The "temporary silicon connection" methodology of Stork provides an example of this approach. See, for example: (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; Kim, G. J. Am. Chem, 1992, 114, 1087. (c) Matsumoto, Y.; Ohno, A.; Hayashi, T. Organametallics 1993, 12, 4051.
22. Aminosilanes are also useful intermediates in the synthesis of bisfunctionalized silanes. See: (a) Stork, G.; Keitz, P. F. Tetrahedron Lett. 1989, 30, 6981. (b) Tamao, K.; Kawachi, A.; Ito, Y. Organometallics 1993, 12, 580.
23. Aminosilanes are also useful intermediates in the synthesis of bisfunctionalized silanes. See: (a) Stork, G.; Keitz, P. F. Tetrahedron Lett. 1989, 30, 6981. (b) Tamao, K.; Kawachi, A.; Ito, Y. Organometallics 1993, 12, 580.
24. (a) George, M. V ; Peterson, D. J.; Gilman, H. J. Am. Chem. Soc. 1960, 82, 403.
25. (b) Fleming, I ; Newton, T. W. J. Chem. Soc., Perkins Trans. 1 1984, 1805.
26. Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29.
27. For a recent report on the isolation of a stable α-trialkylsilyl substituted aldehyde, see: Duhamel, L.; Gralak, J.; Bouyanzer, A. J. Chem. Soc., Chem. Commun. 1993, 1763.
28. Linderman, R. J.; Chen, K. Y. Tetrahedron Lett. 1992, 33, 6767.
29. Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079.
30. Mancuso, A J.; Brownfair, D S ; Swern, D. J. Org. Chem. 1979, 44, 4148.
31. Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779.
32. (a) Imwinkelreid, R.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1985, 24, 591.
33. (b) Mukaiyama, T.; Ohshima, M.; Muyishi, N. Chem. Lett. 1987, 1121.
34. Hoffman, R. W. Chem. Rev. 1989, 89, 1841.
35. Allylsilane additions to unsaturated aldehydes result in mixtures of 1,2- and 1,4-addition products as well as diaddition products; see: Hosomi, A.; Endo, M.; Sakurai, H. Chem. Lett. 1978, 499.
36. Linderman, R. J.; Ghannam, A.; Badejo, I. J. Org. Chem. 1991, 56, 5213.
37. For recent mechanistic investigations into the reaction of nonsilyl-substituted acyclic acetals, see: Sammakia, T.; Smith, R S. J. Am. Chem. Soc. 1994, 116, 7915 and references therein.
38. (a) Hosomi, A.; Kohra, S.; Ogata, K.; Yanagi, T.; Tominaga, Y. J. Org. Chem. 1990, 55, 2415.
39. (b) Hosomi, A ; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987, 1517.
40. (a) Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099.
41. (b) Sato, K.; Kira, M.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 6429.
42. (a) Mohr, P. Tetrahedron Lett. 1993, 34, 6251.
43. (b) For a diastereoselective synthesis of tetrahydrofurans via an intermolecular allylsilane addition, see: Panek, J. S.; Beresis, R. J. Org. Chem. 1993, 58, 809.
44. (a) Marko, I. E., Bailey, M.; Murphy, F.; Declercq, J.-P.; Tinant, B.; Feneau-Dupont, J.; Krief, A.; Dumont, W. Synlett 1995, 123.
45. (b) Marko, I. E.; Bayston, D. J. Tetrahedron 1994, 50, 7141 and earlier references therein.
46. (a) Lee, T. V.; Ellis, K. L.; Richardson, K. A.; Visani, N. Tetrahedron 1989, 45, 1167.
47. (b) Lee, T. V.; Boucher, R. J.; Porter, J. R.; Taylor, D. A. Tetrahedron 1988, 44, 4233.
48. (a) For a review of hyperconjugation effects of silicon, see: Lambert, J. B. Tetrahedron 1990, 46, 2677. For additional recent studies, see: (b) Lambert, J. B.; Emblidge, R. W.; Malany, S. J. Am. Chem. Soc. 1993, 115, 1317. (c) Yoshida, J.; Maekawa, T.; Murata, T.; Matsunaga, S.; Isoe, S. J. Am. Chem. Soc. 1990, 112, 962. (d) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609.
49. (a) For a review of hyperconjugation effects of silicon, see: Lambert, J. B. Tetrahedron 1990, 46, 2677. For additional recent studies, see: (b) Lambert, J. B.; Emblidge, R. W.; Malany, S. J. Am. Chem. Soc. 1993, 115, 1317. (c) Yoshida, J.; Maekawa, T.; Murata, T.; Matsunaga, S.; Isoe, S. J. Am. Chem. Soc. 1990, 112, 962. (d) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609.
50. (a) For a review of hyperconjugation effects of silicon, see: Lambert, J. B. Tetrahedron 1990, 46, 2677. For additional recent studies, see: (b) Lambert, J. B.; Emblidge, R. W.; Malany, S. J. Am. Chem. Soc. 1993, 115, 1317. (c) Yoshida, J.; Maekawa, T.; Murata, T.; Matsunaga, S.; Isoe, S. J. Am. Chem. Soc. 1990, 112, 962. (d) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609.
51. (a) For a review of hyperconjugation effects of silicon, see: Lambert, J. B. Tetrahedron 1990, 46, 2677. For additional recent studies, see: (b) Lambert, J. B.; Emblidge, R. W.; Malany, S. J. Am. Chem. Soc. 1993, 115, 1317. (c) Yoshida, J.; Maekawa, T.; Murata, T.; Matsunaga, S.; Isoe, S. J. Am. Chem. Soc. 1990, 112, 962. (d) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609.
52. A control reaction indicated that the deprotection/reprotection sequence did not effect the diastereomeric ratio of the product.
53. The silica gel must be deactivated by treatment with triethylamine (2%)/hexane prior to chromatography of 28 or 29 (see Experimental Section).
54. Wada, M.; Shigehisa, T.; Kitani, H.; Akiba, K.-Y. Tetrahedron Lett. 1983, 24, 1715.