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. Author manuscript; available in PMC: 2009 Jun 23.
Published in final edited form as: J Org Chem. 2008 May 1;73(11):4017–4026. doi: 10.1021/jo800204n

Table 1.

Catalyzed Asymmetric Reduction of Acetophenone O-Substituted Oxime Ethers

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entry oxime R yield (%)a,b ee (%)c
1 a Me 85 95
2 b Bn 77 97
3 c 4-MeOBn 70 97
4 d 4-CF3Bn 60 99
5 e 2-NO2Bn 95 97
a

Borane was stabilized with <0.005 M N-isopropyl N-methyl tert-butylamine.

b

Isolated yield after purification by column chromatography.

c

The ee was analyzed using a Crompack Chirasil-Dex-CB GC column.