Homochiral Amine Oxides in the Enantioselective Reduction of Ketones

Ian A. O'Neil; Carl D. Turner; S. Barret Kalindjian

doi:10.1055/s-1997-5770

Synlett 1997; 1997(7): 777-780
DOI: 10.1055/s-1997-5770

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Homochiral Amine Oxides in the Enantioselective Reduction of Ketones

Ian A. O'Neil¹ , Carl D. Turner¹ , S. Barret Kalindjian²

¹Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, U.K.
²James Black Foundation, 68 Half Moon Lane, Dulwich, London SE 24 9JE, U.K.

Abstract

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The synthesis of a number of novel homochiral prolinol N-oxide derivatives is described. Several of these were found to catalyse the borane reduction of α-chloroacetophenone to (S)-2-chloro-1-phenylethanol in excellent chemical yield and in 96% ee.

chiral amine oxide - enantioselective reduction - borane - chiral alcohol

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