Title
3-Menthoxybiphenyl-4-carboxylic acid: a versatile resolving agent and reagent for determination of the absolute configuration of benzylic alcohols
Author
Shunsuke Kuwahara, Nobuyoshi Tasaki, Yuri Suzuki, Mizuki Nakagawa, Mari Ikeda, Yoichi Habata
Year
2017
Journal
Tetrahedron: Asymmetry
Abstract
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.
Instrument
J-820
Keywords
Circular dichroism, Absolute configuration, Materials