Paper
Kinetic resolution of racemic alpha-arylalkanoic acids with achiral alcohols via the asymmetric esterification using carboxylic anhydrides and acyl-transfer catalysts.
Published Aug 3, 2010 · Isamu Shiina, Kenya Nakata, K. Ono
Journal of the American Chemical Society
99
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Abstract
A variety of optically active carboxylic esters are produced by the kinetic resolution of racemic alpha-substituted carboxylic acids using achiral alcohols, aromatic or aliphatic carboxylic anhydrides, and chiral acyl-transfer catalysts. The combination of 4-methoxybenzoic anhydride (PMBA) or pivalic anhydride with the modified benzotetramisole-type catalyst ((S)-beta-Np-BTM) is the most effective for promotion of the enantioselective coupling reaction between racemic carboxylic acids and a novel nucleophile, bis(alpha-naphthyl)methanol, to give the corresponding esters with high ee's. This protocol was successfully applied to the production of nonracemic nonsteroidal anti-inflammatory drugs from racemic compounds utilizing the transacylation process to generate the mixed anhydrides from the acid components with the suitable carboxylic anhydrides.
Highly CitedKinetic resolution of racemic alpha-substituted carboxylic acids with achiral alcohols and chiral acyl-transfer catalysts can produce optically active carboxylic esters, potentially benefiting the production of nonracemic nonsteroidal anti-inflammatory drugs.
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