光学活性アミノアルコール・ボラン錯体による触媒的不斉還元

概要

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Reaction of optically active amino alcohol with 2 equiv. of BH<SUB>3</SUB>·THF gave the excellent asymmetric reducing agent, which reduced aromatic ketones, dialkylketones, and oxime ethers to yield chiral secondary alcohols and primary amines, respectively, with high optical yield (>90%ee). Optically active amino alcohols were easily prepared from amino acids. Cross-linked polystyrene supported chiral amino alcohols were also prepared. A polymeric asymmetric reducing agent could realize high enantioselectivity as same as monomeric one with quantitative recover and reuse. Catalytic use of the chiral amino alcohol-borane complex was also investigated on the basis of following behaviours. (1) The reduction with borane was accelerated by the presence of the complex. (2) Large amount of the product was obtained by the use of the small amount of the complex. (3) The product is optically active. (4) The product does not bind to the complex.
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