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Updated: Sep 24, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1'-biaryl-2,2'-diols
Gamal A I Moustafa1,2, Kengo Kasama1, Koichi Higashio1
1Graduate School of Pharmaceutical Sciences, Osaka University 1-6 Yamadaoka Suita, Osaka 565-0871 Japan akai@phs.osaka-u.ac.jp.
Abstract:
Herein we report a dramatic acceleration of the lipase-catalyzed kinetic resolution of atropisomeric 1,1'-biaryl-2,2'-diols by the addition of sodium carbonate. This result likely originates from the increased nucleophilicity of the phenolic hydroxyl group toward the acyl-enzyme intermediate. Under these conditions, various substituted C 2-symmetric and non-C 2-symmetric binaphthols and biphenols were efficiently resolved with ∼50% conversion in only 13-30 h with excellent enantioselectivity.
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