Optically Active Allylsilanes. 2. High Stereoselectivity in Asymmetric Reaction with Aldehydes Producing Homoallylic Alcohols

Journal of the American Chemical Society

Volumn 104, Issue 18, 1982, Pages 4963-4965

  Hayashi, Tamio ^a   Konishi, Mitsuo ^a   Kumada, Makoto ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001506789     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00382a046     Document Type: Article

References (26)

1. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
2. Evans, D. A.; McGee, L. R. J. Am. Chem. Soc. 1981, 103, 2876.
3. Masamune, S.; Choy, W.; Kerdesky, F. A. J.; Imperiali, B. J. Am. Chem. Soc. 1981, 103, 1566.
4. Meyers, A. I.; Yamamoto, Y. J. Am. Chem. Soc. 1981, 103, 4278.
5. See also: Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
6. Heathcock, C. H.; White, C. T.; Morrison, J. J.; VanDerveer, D. J. Org. Chem. 1981, 46, 1296 and references cited therein.
7. Masamune, S.; Ali, Sk. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557.
8. Hoffmann, R. W.; Ladner, W. Tetrahedron Lett. 1979, 4653.
9. Hoffmann, R. W.; Zeiss, H.-J. Angew. Chem., Int. Ed. Engl. 1980, 19, 218.
10. See also: Herold, T.; Schrott, U.; Hoffmann, R. W. Chem. Ber. 1981, 114, 359.
11. Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375.
12. Hayashi, T.; Konishi, M.; Ito, H.; Kumada, M. J. Am. Chem. Soc., preceding paper in this issue.
13. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 1295.
14. Fleming, I.; Paterson, I. Synthesis 1979, 446.
15. Mulzer, J.; Zippel, M.; Bruntrup, G.; Segner, J.; Finke, J.; Liebigs Ann. Chem. 1980, 1108.
16. Maskens, K.; Polgar, N. J. Chem. Soc., Perkin Trans. 1 1973, 109.
17. Tai, A.; Imaida, M. Bull. Chem. Soc. Jpn. 1978, 51, 1114.
18. Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
19. Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106.
20. Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 7107.
21. Chérest, M.; Felkin, H.; Frajerman, C. Tetrahedron Lett. 1971, 379 and their previous papers cited therein.
22. The erythro selectivity of the (E)-allylsilanes may also support the linear transition state and reject the cyclic transition state. See ref 1 and 7. See also: Hoffmann, R. W.; Zeiss, H.-J. J. Org. Chem. 1981, 46, 1309.
23. Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1980, 993.
24. Hiyama, T.; Kimura, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1037.
25. Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1981, 103, 3229.
26. Yamamoto, Y.; Maruyama, K. Tetrahedron Lett. 1981, 22, 2895 and references cited therein.