Asymmetric Reduction of Oxime Ethers Promoted by Chiral Spiroborate Esters with an O3BN Framework

Enatioselective reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework is reported for the first time. In the presence of (R,S)-1, 11 aralkyloxime ethers are reduced by borane−THF at 0−5 °C to give (S)-1-aralkylamine in high yield and excellent enatiomeric excess (up...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-05, Vol.71 (10), p.3998-4001
Main Authors: Chu, Yunbo, Shan, Zixing, Liu, Dejun, Sun, Nannan
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Online Access:Get full text
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Summary:Enatioselective reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework is reported for the first time. In the presence of (R,S)-1, 11 aralkyloxime ethers are reduced by borane−THF at 0−5 °C to give (S)-1-aralkylamine in high yield and excellent enatiomeric excess (up to 98% ee). Influence of reaction conditions on the enantioselectivity of the reduction is investigated, and a possible mechanism of the catalytic reduction is suggested.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060123n