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Resolution of Carboxylic Acids Using Copper(I)-Promoted Removal of Propargylic Esters under Neutral Conditions

  作者 GHOSH PARTHA; AUBE JEFFREY  
  选自 期刊  Journal of Organic Chemistry;  卷期  2011年76-10;  页码  4168-4172  
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[摘要]A method for the optical resolution of carboxylic acids is described. Condensation of racemic carboxylic adds 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 adds 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.

 
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