Solvent-dependent diastereoselectivities in reductions of β-hydroxyketones by Sml2

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2685-2688

  Chopade, Pramod R ^a   Davis, Todd A ^a   Prasad, Edamana ^b   Flowers II, Robert A ^b  

^a TEXAS TECH UNIVERSITY   (United States)

^b LEHIGH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; PROTON;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIASTEREOISOMER; REDUCTION; SOLVATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 4344696825     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049129u     Document Type: Article

References (22)

1. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
2. Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727-2751.
3. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698.
4. Newcomb, M.; Kaplan, J. Tetrahedron Lett. 1988, 29, 3449-3450.
5. Nagashima, T.; Rivkin, A.; Curran, D. P. Can. J. Chem. 2000, 78, 791-799.
6. Namy, J.-L.; Colomb, M.; Kagan, H. B. Tetrahedron Lett. 1994, 35, 1723-1726.
7. Hamann, B.; Namy, J.-L.; Kagan, H. B. Tetrahedron 1996, 52, 14225-14234.
8. Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219-220.
9. Chebolu, V.; Whittle, R. R.; Sen, A. Inorg. Chem. 1985, 24, 3082-3085.
10. Evans W. J.; Broomhall-Dillard, R. N. R.; Ziller, J. W. Polyhedron 1998, 17, 3361-3370.
11. Evans, W. J.; Gummersheimer, T. S.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 8999-9002.
12. Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251-5255.
13. Kuhlman, M. L.; Flowers, R. A., II. Tetrahedron Lett. 2000, 41, 8049-8052.
14. Dorenbos, P. J. Phys.: Conden. Matter 2003, 15, 575-594.
15. Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6357-6361.
16. Keck, G. E.; Wager, C. A.; Sell, T.; Wager, T. T. J. Org. Chem. 1999, 64, 2172-2173.
17. Rychnovsky, S.; Yang, G.; Powers, J. J. Org. Chem., 1993, 58, 5251-5255.
18. (a) Edmonds, D. J.; Muir, K. W.; Procter, D. J. J. Org. Chem. 2003, 68, 3190-3198.
19. (b) Hutton, T. K.; Muir, K. W.; Procter, D. J. Org. Lett. 2003, 5, 4811-4814.
20. Hoz, S.; Yacovan, A.; Bilkis, I. J. Am. Chem. Soc. 1996, 118, 261-262.
21. Chopade, P. R.; Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2004, 126, 44-45.
22. Dahlen, A.; Hilmersson, G.; Knettle, B. W.; Flowers, R. A., II. J. Org. Chem. 2003, 68, 4870-4875.