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Communication | Special issue | Vol 80, No. 1, 2010, pp.169-175
Published online, 6th August, 2009
DOI: 10.3987/COM-09-S(S)43
An Effective Kinetic Resolution of Racemic Secondary Benzylic Alcohols Using 3-Pyridinecarboxylic Anhydride and a Chiral Acyl-Transfer Catalyst in the Absence of Tertiary Amine

Kenya Nakata and Isamu Shiina*

*Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan


3-Pyridinecarboxylic anhydride (3-PCA) was found to function as an efficient coupling reagent for the kinetic resolution of racemic secondary benzylic alcohols with achiral carboxylic acids in the presence of a catalytic amount of (+)-BTM. A variety of optically active carboxylic esters are produced with high enantiomeric excesses by this new chiral induction system without using a tertiary amine.