Asymmetric hydrogenation of quinoxalines with diphosphinite ligands: A practical synthesis of enantioenriched, substituted tetrahydroquinoxalines

Weijun Tang; Lijin Xu; Qing Hua Fan; Jun Wang; Baomin Fan; Zhongyuan Zhou; Kim Hung Lam; Albert S.C. Chan

doi:10.1002/anie.200904518

Asymmetric hydrogenation of quinoxalines with diphosphinite ligands: A practical synthesis of enantioenriched, substituted tetrahydroquinoxalines

Weijun Tang, Lijin Xu, Qing Hua Fan, Jun Wang, Baomin Fan, Zhongyuan Zhou, Kim Hung Lam, Albert S.C. Chan

Research output: Journal article publication › Journal article › Academic research › peer-review

122 Citations (Scopus)

Abstract

An easily accessible chiral lr/H₈-binapo catalyst exhibits unprecedented reactivity and excellent enantioselectivity in the hydrogenation of quinoxalines at a high ratio of substrate to catalyst (from 100 to 20000). This new method provides a practical synthetic approach to give optically active chiral tetrahydroquinoxaline derivatives (see scheme; cod = l, 5-cyclooctadiene).

Original language	English
Pages (from-to)	9135-9138
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	48
DOIs	https://doi.org/10.1002/anie.200904518
Publication status	Published - 16 Nov 2009

Keywords

Asymmetric catalysis
Diphosphinite ligands
Hydrogenation
Tetrahydroquinoxalines

ASJC Scopus subject areas

Catalysis
Chemistry(all)

More information

10.1002/anie.200904518

Cite this

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title = "Asymmetric hydrogenation of quinoxalines with diphosphinite ligands: A practical synthesis of enantioenriched, substituted tetrahydroquinoxalines",

abstract = "An easily accessible chiral lr/H8-binapo catalyst exhibits unprecedented reactivity and excellent enantioselectivity in the hydrogenation of quinoxalines at a high ratio of substrate to catalyst (from 100 to 20000). This new method provides a practical synthetic approach to give optically active chiral tetrahydroquinoxaline derivatives (see scheme; cod = l, 5-cyclooctadiene).",

keywords = "Asymmetric catalysis, Diphosphinite ligands, Hydrogenation, Tetrahydroquinoxalines",

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Asymmetric hydrogenation of quinoxalines with diphosphinite ligands : A practical synthesis of enantioenriched, substituted tetrahydroquinoxalines. / Tang, Weijun; Xu, Lijin; Fan, Qing Hua et al.

In: Angewandte Chemie - International Edition, Vol. 48, No. 48, 16.11.2009, p. 9135-9138.

Research output: Journal article publication › Journal article › Academic research › peer-review

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T1 - Asymmetric hydrogenation of quinoxalines with diphosphinite ligands

T2 - A practical synthesis of enantioenriched, substituted tetrahydroquinoxalines

AU - Tang, Weijun

AU - Xu, Lijin

AU - Fan, Qing Hua

AU - Wang, Jun

AU - Fan, Baomin

AU - Zhou, Zhongyuan

AU - Lam, Kim Hung

AU - Chan, Albert S.C.

PY - 2009/11/16

Y1 - 2009/11/16

N2 - An easily accessible chiral lr/H8-binapo catalyst exhibits unprecedented reactivity and excellent enantioselectivity in the hydrogenation of quinoxalines at a high ratio of substrate to catalyst (from 100 to 20000). This new method provides a practical synthetic approach to give optically active chiral tetrahydroquinoxaline derivatives (see scheme; cod = l, 5-cyclooctadiene).

AB - An easily accessible chiral lr/H8-binapo catalyst exhibits unprecedented reactivity and excellent enantioselectivity in the hydrogenation of quinoxalines at a high ratio of substrate to catalyst (from 100 to 20000). This new method provides a practical synthetic approach to give optically active chiral tetrahydroquinoxaline derivatives (see scheme; cod = l, 5-cyclooctadiene).

KW - Asymmetric catalysis

KW - Diphosphinite ligands

KW - Hydrogenation

KW - Tetrahydroquinoxalines

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M3 - Journal article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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Asymmetric hydrogenation of quinoxalines with diphosphinite ligands: A practical synthesis of enantioenriched, substituted tetrahydroquinoxalines

Abstract

Keywords

ASJC Scopus subject areas

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