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

Gamal A.I. Moustafa; Kengo Kasama; Koichi Higashio; Shuji Akai

doi:10.1039/c8ra09070j

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

Gamal A.I. Moustafa, Kengo Kasama, Koichi Higashio, Shuji Akai^*

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

23 被引用数 (Scopus)

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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.

本文言語	英語
ページ（範囲）	1165-1175
ページ数	11
ジャーナル	RSC Advances
巻	9
号	3
DOI	https://doi.org/10.1039/c8ra09070j
出版ステータス	出版済み - 2019

ASJC Scopus 主題領域

化学一般
化学工学一般

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10.1039/c8ra09070j

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title = "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.",

author = "Moustafa, {Gamal A.I.} and Kengo Kasama and Koichi Higashio and Shuji Akai",

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year = "2019",

doi = "10.1039/c8ra09070j",

language = "英語",

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T1 - Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols

AU - Moustafa, Gamal A.I.

AU - Kasama, Kengo

AU - Higashio, Koichi

AU - Akai, Shuji

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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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U2 - 10.1039/c8ra09070j

DO - 10.1039/c8ra09070j

M3 - 学術論文

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JO - RSC Advances

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

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