Oxidative and enantioselective cross-coupling of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether

Yujiro Hayashi; Takahiko Itoh; Hayato Ishikawa

doi:10.1002/anie.201006885

Oxidative and enantioselective cross-coupling of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether

Yujiro Hayashi, Takahiko Itoh, Hayato Ishikawa

研究成果: Article › 査読

111 被引用数 (Scopus)

抄録

Synthetically important β-substituted γ-nitro aldehydes have been synthesized with excellent enantioselectivity by the cross-coupling reaction of β-aryl substituted aldehydes or Y γ-unsaturated aldehydes and nitromethane using 2,3-dichloro-5,6-dicyanoquinone (DDQ) and diphenylprolinol silyl ether as an oxidant and catalyst, respectively (see scheme; TMS=trimethylsilyl).

本文言語	English
ページ（範囲）	3920-3924
ページ数	5
ジャーナル	Angewandte Chemie - International Edition
巻	50
号	17
DOI	https://doi.org/10.1002/anie.201006885
出版ステータス	Published - 2011 4 18
外部発表	はい

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化学 (全般)

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title = "Oxidative and enantioselective cross-coupling of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether",

abstract = "Synthetically important β-substituted γ-nitro aldehydes have been synthesized with excellent enantioselectivity by the cross-coupling reaction of β-aryl substituted aldehydes or Y γ-unsaturated aldehydes and nitromethane using 2,3-dichloro-5,6-dicyanoquinone (DDQ) and diphenylprolinol silyl ether as an oxidant and catalyst, respectively (see scheme; TMS=trimethylsilyl).",

keywords = "asymmetric catalysis, cross-coupling, one-pot reaction, organocatalysis, oxidative reaction",

author = "Yujiro Hayashi and Takahiko Itoh and Hayato Ishikawa",

year = "2011",

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doi = "10.1002/anie.201006885",

language = "English",

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journal = "Angewandte Chemie - International Edition",

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T1 - Oxidative and enantioselective cross-coupling of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether

AU - Hayashi, Yujiro

AU - Itoh, Takahiko

AU - Ishikawa, Hayato

PY - 2011/4/18

Y1 - 2011/4/18

N2 - Synthetically important β-substituted γ-nitro aldehydes have been synthesized with excellent enantioselectivity by the cross-coupling reaction of β-aryl substituted aldehydes or Y γ-unsaturated aldehydes and nitromethane using 2,3-dichloro-5,6-dicyanoquinone (DDQ) and diphenylprolinol silyl ether as an oxidant and catalyst, respectively (see scheme; TMS=trimethylsilyl).

AB - Synthetically important β-substituted γ-nitro aldehydes have been synthesized with excellent enantioselectivity by the cross-coupling reaction of β-aryl substituted aldehydes or Y γ-unsaturated aldehydes and nitromethane using 2,3-dichloro-5,6-dicyanoquinone (DDQ) and diphenylprolinol silyl ether as an oxidant and catalyst, respectively (see scheme; TMS=trimethylsilyl).

KW - asymmetric catalysis

KW - cross-coupling

KW - one-pot reaction

KW - organocatalysis

KW - oxidative reaction

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DO - 10.1002/anie.201006885

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EP - 3924

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

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Oxidative and enantioselective cross-coupling of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether

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