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. 2006 May 12;71(10):3998-4001.
doi: 10.1021/jo060123n.

Asymmetric reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework

Yunbo Chu  1 , Zixing Shan, Dejun Liu, Nannan Sun
Affiliations

Asymmetric reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework

Yunbo Chu et al. J Org Chem. .

Abstract

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 degrees 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.

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