3-Menthoxybiphenyl-4-carboxylic acid: a versatile resolving agent and reagent for determination of the absolute configuration of benzylic alcohols

Add time:07/17/2019    Source:sciencedirect.com

A versatile reagent for the chiral resolution and determination of the absolute configuration of benzylic alcohols, (−)-3-menthoxybiphenyl-4-carboxylic acid, is reported. (−)-3-menthoxybiphenyl-4-carboxylic acid was condensed with racemic benzylic alcohols to yield diastereomeric 3-menthoxybiphenyl-4-carboxylic esters, which were separated by reversed-phase HPLC. The absolute configurations of the 3-menthoxybiphenyl-4-carboxylic esters were unambiguously determined by exciton-coupled circular dichroism. Hydrolysis of the 3-menthoxybiphenyl-4-carboxylic esters yielded enantiopure alcohols, and their absolute configurations were simultaneously determined.

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