Development of Kinetic Resolution of Racemic Alcohols and Carboxylic Acids Accompanied with Dehydration Condensation

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  • Shiina Isamu
    Department of Chemistry, Faculty of Science, Tokyo University of Science
  • Nakata Kenya
    Interdisciplinary Graduate School of Science and Engineering, Shimane University

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  • 脱水縮合を伴う速度論的光学分割反応の開発
  • ダッスイ シュクゴウ オ トモナウ ソクドロンテキ コウガク ブンカツ ハンノウ ノ カイハツ

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Abstract

A novel and efficient method for the kinetic resolution of racemic alcohols with achiral carboxylic acids or racemic carboxylic acids with achiral alcohols using dehydration condensation is accounted in this paper. The first kinetic resolution of racemic alcohols with achiral carboxylic acids was accomplished by asymmetric esterification via the in situ formation of a mixed anhydride using carboxylic anhydrides as coupling reagents in the presence of chiral acyl-transfer catalysts. Because this protocol utilized the transacylation process to generate the mixed-anhydride, not only racemic secondary alcohols but also racemic carboxylic acids are applicable to the asymmetric esterification in the same manner. The variety of optically active carboxylic esters are also produced by the kinetic resolution of racemic 2-arylalkanoic acids, including non-steroidal anti-inflammatory drugs (NSAIDs), with achiral alcohols, using carboxylic anhydrides in the presence of chiral acyl-transfer catalysts.

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