Reexamination of aluminum hydride as a stereoselective reducing agent for reduction of cyclic ketones to thermodynamically more stable alcohols

Bulletin of the Korean Chemical Society

Volumn 21, Issue 1, 2000, Pages 128-130

  Cha, Jin Soon ^a   Moon, Suk Joung ^a   Kwon, Oh Oun ^a   Lee, Yong Rok ^a  

^a Yeungnam University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALUMINUM; CAMPHOR; CYCLOHEXANONE; KETONE;

ARTICLE; CHEMICAL ANALYSIS; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0001531790     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Some examples: (a) Ellefson, C. R.; Cusic, J. W. J. Med. Chem. 1976, 19, 1345.
2. (b) Martinez, E.; Muchowski, J. M.; Velarde, E. J. Org. Chem. 1977, 42, 1087.
3. (c) Packer, R. A.; Whitehurst, J. S. J. Chem. Soc., Perkin Trans. 1 1978, 110.
4. (d) Jacob, P., III; Kline, T.; Castagnoli, N. Jr. J. Med. Chem. 1979, 22, 662.
5. (e) Martin, S. F.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170.
6. (f) Pratt, J. A. E.; Sutherland, I. O.; Newton, R. F. J. Chem. Soc., Perkin Trans. 1 1998, 13.
7. Jorgenson, M. J. Tetrahedron Lett. 1962, 559.
8. (a) Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464.
9. (b) Yoon, N. M.; Brown, H. C. Ibid. 1968, 90, 2927.
10. Cha, J. S.; Kwon, O. O.; Kim, J. M.; Cho, S. D. Synlett 1997, 1465.
11. (a) Cha, J. S.; Kwon, O. O. J. Org. Chem. 1997, 62, 3209.
12. (b) Haubenstock, H.; Davidson, E. B. Ibid. 1963, 28, 2772.
13. For comprehensive reviews, see: (a) Bruno, G. The Use of Aluminum Alkyls in Organic Synthesis; Ethyl Corp.: Baton Rouge, LA, 1968.
14. (b) Bruno, G. The Use of Aluminum Alkyls in Organic Synthesis; 1969-1972.
15. (c) Winterfeldt, E. Synthesis 1975, 617.
16. (a) Ashby, E. C.; Yu, S. H. J. Org. Chem. 1970, 35, 1034.
17. (b) Heinsohn, G. E.; Ashby, E. C. Ibid. 1973, 38, 4232.
18. (a) Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464.
19. (b) Yoon, N. M.; Brown, H. C. Ibid. 1968, 90, 2927.
20. (c) Cha, J. S.; Brown, H. C. J. Org. Chem. 1993, 58, 3974.