An especially convenient stereoselective reduction of β-hydroxy ketones to anti 1,3 diols using samarium diiodide

Journal of Organic Chemistry

Volumn 64, Issue 7, 1999, Pages 2172-2173

  Keck, Gary E ^a   Wager, Carrie A ^a   Sell, Thorsten ^a   Wager, Travis T ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; SAMARIUM;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; OXIDATION REDUCTION REACTION;

EID: 0033515504     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982428a     Document Type: Article

References (9)

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3. (b) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem. Lett. 1987, 1923.
4. Paterson, I.; Channon, J. A. Tetrahedron Lett. 1992, 33, 797.
5. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
6. Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
7. Selective reduction of ketones that lack an α substituent is especially problematic; for a recent case study, see: Watanabe, H.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 1998, 39, 8313.
8. Structural assignments were based upon independent synthesis and also spectral analysis of the derived acetonides using the method of Rychnovsky: Rychnovsky, S. D.; Yang, G.; Powers, J. P. J. Org. Chem. 1993, 58, 5251.
9. 2 reductions that this substrate is reduced with a high degree of stereoselectivity.