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Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1'-biaryl-2,2'-diols.

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.

SUBMITTER: Moustafa GAI

PROVIDER: S-EPMC9059663 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1'-biaryl-2,2'-diols.

Moustafa Gamal A I GAI Kasama Kengo K Higashio Koichi K Akai Shuji S

RSC advances 20190109 3

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 w ...[more]

PMID: 35518007

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