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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.
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Publication Date:
31 December 2000 (online)

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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