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Resolution of carboxylic acids using copper(I)-promoted removal of propargylic esters under neutral conditions.

ABSTRACT: A method for the optical resolution of carboxylic acids is described. Condensation of racemic carboxylic acids with chiral terminal propargyl alcohols gave separable diastereomeric esters. Chromatographic separation followed by heating the individual diastereomers in methanol with catalytic copper(I) halide regenerated the carboxylic acids in good yields and in enantiomeric ratios of ?94%. This method is particularly useful for the resolution of carboxylic acids that are incompatible with conventional ester hydrolysis.

SUBMITTER: Ghosh P 

PROVIDER: S-EPMC3691273 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Resolution of carboxylic acids using copper(I)-promoted removal of propargylic esters under neutral conditions.

Ghosh Partha P   Aubé Jeffrey J  

The Journal of organic chemistry 20110414 10

A method for the optical resolution of carboxylic acids is described. Condensation of racemic carboxylic acids with chiral terminal propargyl alcohols gave separable diastereomeric esters. Chromatographic separation followed by heating the individual diastereomers in methanol with catalytic copper(I) halide regenerated the carboxylic acids in good yields and in enantiomeric ratios of ≥94%. This method is particularly useful for the resolution of carboxylic acids that are incompatible with conven  ...[more]

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