Homochiral amine oxides in the enantioselective reduction of ketones

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 alpha-chloroacetophenone to (S)-2-chloro-1-phenylethanol in excellent chemical yield and in 96% ee.

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Bibliographic Details
Published inSynlett no. 7; pp. 777 - 781
Main Authors ONeil, IA, Turner, CD, Kalindjian, SB
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.1997
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
chiral amine oxide
enantioselective reduction
chiral alcohol
N-OXIDES
COMPLEXES
borane
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Summary: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 alpha-chloroacetophenone to (S)-2-chloro-1-phenylethanol in excellent chemical yield and in 96% ee.
ISSN:0936-5214
DOI:10.1055/s-1997-5770