Asymmetric hydrogenation of quinolines with recyclable and air-stable iridium catalyst systems

Sau Hing Chan; Kim Hung Lam; Yue Ming Li; Lijin Xu; Weijun Tang; Fuk Loi Lam; Wai Hung Lo; Wing Yiu Yu; Qinghua Fan; Albert S.C. Chan

doi:10.1016/j.tetasy.2007.10.034

Asymmetric hydrogenation of quinolines with recyclable and air-stable iridium catalyst systems

Sau Hing Chan, Kim Hung Lam, Yue Ming Li, Lijin Xu, Weijun Tang, Fuk Loi Lam, Wai Hung Lo, Wing Yiu Yu, Qinghua Fan, Albert S.C. Chan

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

45 Citations (Scopus)

Abstract

The iridium complex-catalyzed asymmetric hydrogenation of quinolines in a DMPEG/hexane biphasic system was studied. Catalysts with C2-symmetric ligands such as Xyl-P-Phos, Cl-MeO-BIPHEP, SYNPHOS, and DifluorPhos are highly effective for this type of reaction. Most of the catalysts tested can be retained in DMPEG (Mn= 500), and the asymmetric hydrogenation of various quinoline substrates can be carried out in DMPEG/hexane biphasic system with up to 92% ee. The catalysts and the products can be separated via simple phase separation, and the reactivity/stereoselectivity of the catalysts can be retained for at least three reaction cycles.

Original language	English
Pages (from-to)	2625-2631
Number of pages	7
Journal	Tetrahedron Asymmetry
Volume	18
Issue number	22
DOIs	https://doi.org/10.1016/j.tetasy.2007.10.034
Publication status	Published - 12 Nov 2007
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2007.10.034

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title = "Asymmetric hydrogenation of quinolines with recyclable and air-stable iridium catalyst systems",

abstract = "The iridium complex-catalyzed asymmetric hydrogenation of quinolines in a DMPEG/hexane biphasic system was studied. Catalysts with C2-symmetric ligands such as Xyl-P-Phos, Cl-MeO-BIPHEP, SYNPHOS, and DifluorPhos are highly effective for this type of reaction. Most of the catalysts tested can be retained in DMPEG (Mn= 500), and the asymmetric hydrogenation of various quinoline substrates can be carried out in DMPEG/hexane biphasic system with up to 92% ee. The catalysts and the products can be separated via simple phase separation, and the reactivity/stereoselectivity of the catalysts can be retained for at least three reaction cycles.",

author = "Chan, {Sau Hing} and Lam, {Kim Hung} and Li, {Yue Ming} and Lijin Xu and Weijun Tang and Lam, {Fuk Loi} and Lo, {Wai Hung} and Yu, {Wing Yiu} and Qinghua Fan and Chan, {Albert S.C.}",

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T1 - Asymmetric hydrogenation of quinolines with recyclable and air-stable iridium catalyst systems

AU - Chan, Sau Hing

AU - Lam, Kim Hung

AU - Li, Yue Ming

AU - Xu, Lijin

AU - Tang, Weijun

AU - Lam, Fuk Loi

AU - Lo, Wai Hung

AU - Yu, Wing Yiu

AU - Fan, Qinghua

AU - Chan, Albert S.C.

PY - 2007/11/12

Y1 - 2007/11/12

N2 - The iridium complex-catalyzed asymmetric hydrogenation of quinolines in a DMPEG/hexane biphasic system was studied. Catalysts with C2-symmetric ligands such as Xyl-P-Phos, Cl-MeO-BIPHEP, SYNPHOS, and DifluorPhos are highly effective for this type of reaction. Most of the catalysts tested can be retained in DMPEG (Mn= 500), and the asymmetric hydrogenation of various quinoline substrates can be carried out in DMPEG/hexane biphasic system with up to 92% ee. The catalysts and the products can be separated via simple phase separation, and the reactivity/stereoselectivity of the catalysts can be retained for at least three reaction cycles.

AB - The iridium complex-catalyzed asymmetric hydrogenation of quinolines in a DMPEG/hexane biphasic system was studied. Catalysts with C2-symmetric ligands such as Xyl-P-Phos, Cl-MeO-BIPHEP, SYNPHOS, and DifluorPhos are highly effective for this type of reaction. Most of the catalysts tested can be retained in DMPEG (Mn= 500), and the asymmetric hydrogenation of various quinoline substrates can be carried out in DMPEG/hexane biphasic system with up to 92% ee. The catalysts and the products can be separated via simple phase separation, and the reactivity/stereoselectivity of the catalysts can be retained for at least three reaction cycles.

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DO - 10.1016/j.tetasy.2007.10.034

M3 - Journal article

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

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ER -

Asymmetric hydrogenation of quinolines with recyclable and air-stable iridium catalyst systems

Abstract

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