Lipase-catalyzed Kinetic Resolution of C1-symmetric heterocyclic biaryls
Lipase-catalyzed Kinetic Resolution of C1-symmetric heterocyclic biaryls
The highly enantioselective lipase-catalyzed kinetic resolution (KR) of racemic C1-symmetric biaryl compounds including heterocyclic moieties, such as carbazole and dibenzofuran, has been achieved for the first time. This enzymatic esterification was accelerated by the addition of disodium carbonate while maintaining its high enantioselectivities, and was particularly effective for biaryls having N-substituted carbazole moieties. Furthermore, mesoporous silica-supported oxovanadium-catalyzed cross-dehydrogenative coupling of 3-hydroxycarbazole and 2-naphthol was followed by the lipase-catalyzed KR in one-pot to synthesize the optically active heterocyclic biaryl compounds with high optical purity.
C1-symmetric biaryl, carbazole, kinetic resolution, lipase, one-pot reaction
391-399
Kasama, Kengo
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Hinami, Yuya
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Mizuno, Karin
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Horino, Satoshi
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Nishio, Tomoya
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Yuki, Chiharu
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Kanomata, Kyohei
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Moustafa, Gamal
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Gröger, Harald
cd0aa4ab-4495-4dc6-a5a5-38ee39376445
Akai, Shuji
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1 May 2022
Kasama, Kengo
7072b264-2420-45fb-aac5-fc116dda3fe6
Hinami, Yuya
2e5695b2-ff0f-4d73-989f-58f1971d8a5a
Mizuno, Karin
b6087063-f97d-4078-81e2-ffd621284276
Horino, Satoshi
94a79810-33a3-4614-bb22-620d1f943072
Nishio, Tomoya
87bac6d3-f8cb-48d9-b249-5b91e4b6eb75
Yuki, Chiharu
ad370f60-a151-4872-8b1a-8dcb5f38bf96
Kanomata, Kyohei
49abfcea-63f3-4c8e-8e96-a0cd943be682
Moustafa, Gamal
1a452cdc-4856-4243-9864-b391fb115f07
Gröger, Harald
cd0aa4ab-4495-4dc6-a5a5-38ee39376445
Akai, Shuji
fa7e6632-d178-4429-ac1b-74930a7f207a
Kasama, Kengo, Hinami, Yuya, Mizuno, Karin, Horino, Satoshi, Nishio, Tomoya, Yuki, Chiharu, Kanomata, Kyohei, Moustafa, Gamal, Gröger, Harald and Akai, Shuji
(2022)
Lipase-catalyzed Kinetic Resolution of C1-symmetric heterocyclic biaryls.
Chemical and Pharmaceutical Bulletin, 70 (5), .
(doi:10.1248/cpb.c22-00021).
Abstract
The highly enantioselective lipase-catalyzed kinetic resolution (KR) of racemic C1-symmetric biaryl compounds including heterocyclic moieties, such as carbazole and dibenzofuran, has been achieved for the first time. This enzymatic esterification was accelerated by the addition of disodium carbonate while maintaining its high enantioselectivities, and was particularly effective for biaryls having N-substituted carbazole moieties. Furthermore, mesoporous silica-supported oxovanadium-catalyzed cross-dehydrogenative coupling of 3-hydroxycarbazole and 2-naphthol was followed by the lipase-catalyzed KR in one-pot to synthesize the optically active heterocyclic biaryl compounds with high optical purity.
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More information
Accepted/In Press date: 25 February 2022
Published date: 1 May 2022
Additional Information:
Publisher Copyright:
© 2022 The Pharmaceutical Society of Japan.
Keywords:
C1-symmetric biaryl, carbazole, kinetic resolution, lipase, one-pot reaction
Identifiers
Local EPrints ID: 457217
URI: http://eprints.soton.ac.uk/id/eprint/457217
ISSN: 1347-5223
PURE UUID: 633927ab-a979-4c70-bba6-97be2093a261
Catalogue record
Date deposited: 26 May 2022 16:50
Last modified: 06 Jun 2024 02:05
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Contributors
Author:
Kengo Kasama
Author:
Yuya Hinami
Author:
Karin Mizuno
Author:
Satoshi Horino
Author:
Tomoya Nishio
Author:
Chiharu Yuki
Author:
Kyohei Kanomata
Author:
Harald Gröger
Author:
Shuji Akai
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