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

Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols
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 these conditions, various substituted C2-symmetric and non-C2-symmetric binaphthols and biphenols were efficiently resolved with ∼50% conversion in only 13–30 h with excellent enantioselectivity.
2046-2069
1165-1175
Moustafa, Gamal A. I.
1a452cdc-4856-4243-9864-b391fb115f07
Kasama, Kengo
7072b264-2420-45fb-aac5-fc116dda3fe6
Higashio, Koichi
6f062c83-a3db-44b1-80fa-5a74e09ac28f
Akai, Shuji
fa7e6632-d178-4429-ac1b-74930a7f207a
Moustafa, Gamal A. I.
1a452cdc-4856-4243-9864-b391fb115f07
Kasama, Kengo
7072b264-2420-45fb-aac5-fc116dda3fe6
Higashio, Koichi
6f062c83-a3db-44b1-80fa-5a74e09ac28f
Akai, Shuji
fa7e6632-d178-4429-ac1b-74930a7f207a

Moustafa, Gamal A. I., Kasama, Kengo, Higashio, Koichi and Akai, Shuji (2019) Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols. RSC Advances, 9, 1165-1175. (doi:10.1039/C8RA09070J).

Record type: Article

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 C2-symmetric and non-C2-symmetric binaphthols and biphenols were efficiently resolved with ∼50% conversion in only 13–30 h with excellent enantioselectivity.

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Accepted/In Press date: 24 December 2018
Published date: 9 January 2019

Identifiers

Local EPrints ID: 427521
URI: https://eprints.soton.ac.uk/id/eprint/427521
ISSN: 2046-2069
PURE UUID: 4f5deeb7-7b39-4962-946e-0793c5b6b6b3

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Date deposited: 22 Jan 2019 17:30
Last modified: 13 Mar 2019 17:39

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Contributors

Author: Kengo Kasama
Author: Koichi Higashio
Author: Shuji Akai

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