Asymmetric Synthesis of Functionalized Tertiary Homoallyl Alcohols by Diastereoselective Allylation of Chiral a-Keto Amides Derived from (S)-Proline Esters. Control of Stereochemistry Based on Saturated Coordination of Lewis Acid

Journal of Organic Chemistry

Volumn 51, Issue 17, 1986, Pages 3290-3295

  Soai, Kenso ^a   Ishizaki, Miyuki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001501419     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00367a008     Document Type: Article

References (48)

1. Morrison, J.D.; Mosher, H.S. Asymmetric Organic Reactions; Prentice-Hall: Englewood-Cliffs, NJ, 1971.
2. Valentine, D., Jr.; Scott, J.W. Synthesis 1978, 329.
3. Kagan, H.B.; Fiaud, J.C. Top. Stereochem. 1978, 10, 175.
4. ApSimon, J.W.; Seguin, R.P. Tetrahedron 1979, 35, 2797.
5. Brown, H.C.; Jadhav, P.K. J. Am. Chem. Soc. 1983, 105, 2092.
6. Herold, T.; Hoffmann, R.W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768.
7. Herold, T.; Schrott, U.; Hoffmann, R.W. Chem. Ber. 1981, 114, 359.
8. Hoffmann, R.W.; Herold, T. Chem. Ber. 1981, 114, 375.
9. Hayashi, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4963; (f) J. Org. Chem. 1983, 48, 281.
10. Otera, J.; Kawasaki, Y.; Mizuno, H.; Shimizu, Y. Chem. Lett. 1983, 1529.
11. Otera, J.; Yoshinaga, Y.; Yamaji, T.; Yoshioka, T.; Kawasaki, Y. Organometallics 1985, 4, 1213.
12. Mukaiyama, T.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem. Lett. 1986, 97.
13. Kiyooka, S.; Heathcock, C.H. Tetrahedron Lett. 1983, 25, 4765
14. Reetz, M.T.; Jung, A. J. Am. Chem. Soc. 1983, 105, 4833.
15. Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489.
16. Heathcock, C.H.; Kiyooka, S.; Blumenkopf, T.A. J. Org. Chem. 1984, 49, 4214.
17. Ojima, I.; Miyazawa, Y.; Kumagai, M. J. Chem. Soc., Chem. Commun. 1976, 927.
18. Boireau, G.; Korenova, A.; Deberly, A; Abenhaim, D. Tetrahedron Lett. 1985, 26, 4181.
19. Johnson, W.S.; Crackett, P.H.; Elliott, J.D.; Jagodzinski, J.J.; Lindell, S.D.; Natarajan, S. Tetrahedron Lett. 1984, 25, 3951.
20. Eliel, E.L.; Koskimies, J.K.; Lohri, B.; Frazee, W.J.; Morris-Natschke, S.; Lynch, J.E.; Soai, K. ACS Symp. Ser. 1981, No. 185.
21. Eliel, E.L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937.
22. Lynch, J.E.; Eliel, E.L. J. Am. Chem. Soc. 2943.
23. Mukaiyama, T.; Sakito, Y.; Asami, M. Chem. Lett. 1978, 1253
24. Mukaiyama, T.; Sakito, Y.; Asami, M. Chem. Lett. 1979, 705.
25. Sakito, Y.; Mukaiyama, T. Chem. Lett. 1979, 1027.
26. Sakito, Y.; Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 455.
27. Enders, D.; Lotter, H. Angew. Chem., Int. Ed. Engl. 1981, 20, 795.
28. Soai, K.; Ookawa, A.; Nohara, Y. Synth. Commun. 1983, 13, 27.
29. Soai, K.; Machida, H.; Ookawa, A. J. Chem. Soc., Chem. Commun. 1985, 469.
30. Soai, K.; Ookawa, A. J. Chem. Soc., Perkin Trans. 1 1986, 759.
31. Soai, K.; Yamanoi, T.; Oyamada, H. Chem. Lett. 1984, 251.
32. Soai, K.; Oyamada, H.; Yamanoi, T. J. Chem. Soc., Chem. Commun. 1984, 413.
33. Soai, K.; Yamanoi, T.; Hikima, H.; Oyamada, H. J. Chem. Soc., Chem. Commun. 1985, 138.
34. Soai, K.; Yamanoi, T.; Hikima, H. J. Organomet. Chem. 1985, 290, C23.
35. Soai, K.; Komiya, K.; Shigematsu, Y.; Hasegawa, H.; Ookawa, A. J. Chem. Soc., Chem. Commun. 1982, 1282.
36. Soai, K.; Hasegawa, H. J. Chem. Soc., Perkin Trans. 1 1985, 769.
37. Soai, K.; Ishizaki, M. J. Chem. Soc., Chem. Commun. 1984, 1016.
38. Hartman, G.D.; Traylor, T.G. Tetrahedron Lett. 1975, 939.
39. Weidner, U.; Schweig, A. J. Organomet. Chem. 1972, 39, 261.
40. Brown, R.S.; Eaton, D.F.; Hosomi, A.; Traylor, T.G.; Wright, J.M. J. Organomet. Chem. 1974, 66, 249.
41. Ueki, M.; Inazu, T. Chem. Lett. 1982, 45.
42. Frater, G.Y.; Müller, U.; Gunther, W. Tetrahedron Lett. 1981, 22 4221.
43. Ohrt, J.; Horeau, A.; Vigneron, J.P.; Kagan, H.B. Tetrahedron 1970, 20, 4705.
44. Eliel, E.L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
45. Abel, E.W.; Rowley, R.J. J. Organomet. Chem. 1975, 84, 199.
46. Watson, S.C.; Eastham, J.F. J. Organomet. Chem. 1967, 9, 165.
47. Gorden, A.J.; Ford, R.A., Eds.; Wiley: New York, 1972.
48. Chantrapromma, K.; Ollis, W.D.; Sutherland, I.O. J. Chem. Soc., Perkin Trans. 1 1983, 1049.