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

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...

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Detalles Bibliográficos
Autores principales: Moustafa, Gamal A. I., Kasama, Kengo, Higashio, Koichi, Akai, Shuji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9059663/
https://www.ncbi.nlm.nih.gov/pubmed/35518007
http://dx.doi.org/10.1039/c8ra09070j
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author Moustafa, Gamal A. I.
Kasama, Kengo
Higashio, Koichi
Akai, Shuji
author_facet Moustafa, Gamal A. I.
Kasama, Kengo
Higashio, Koichi
Akai, Shuji
author_sort Moustafa, Gamal A. I.
collection PubMed
description 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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spelling pubmed-90596632022-05-04 Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols Moustafa, Gamal A. I. Kasama, Kengo Higashio, Koichi Akai, Shuji RSC Adv Chemistry 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. The Royal Society of Chemistry 2019-01-09 /pmc/articles/PMC9059663/ /pubmed/35518007 http://dx.doi.org/10.1039/c8ra09070j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Moustafa, Gamal A. I.
Kasama, Kengo
Higashio, Koichi
Akai, Shuji
Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols
title Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols
title_full Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols
title_fullStr Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols
title_full_unstemmed Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols
title_short Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols
title_sort base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9059663/
https://www.ncbi.nlm.nih.gov/pubmed/35518007
http://dx.doi.org/10.1039/c8ra09070j
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AT kasamakengo basepromotedlipasecatalyzedkineticresolutionofatropisomeric11biaryl22diols
AT higashiokoichi basepromotedlipasecatalyzedkineticresolutionofatropisomeric11biaryl22diols
AT akaishuji basepromotedlipasecatalyzedkineticresolutionofatropisomeric11biaryl22diols

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