Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 10, Pages 3998-4001Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo060123n
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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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