Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations

Hong Yee Cheung; Wing Yiu Yu; Terry T.L. Au-Yeung; Zhongyuan Zhou; Albert S.C. Chan

doi:10.1002/adsc.200900086

Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations

Hong Yee Cheung, Wing Yiu Yu, Terry T.L. Au-Yeung, Zhongyuan Zhou, Albert S.C. Chan

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

41 Citations (Scopus)

Abstract

Chiral ferrocene-derived phosphine-thioether mixed donor ligands supported by heterocycles effected the palladium-catalyzed enantioselective allylic alkylations with excellent yields and enantioselectivities (up to 96% ee). With cyclic and unsymmetrical allylic acetates as substrate, the corresponding alkylated products with enantioselectivities up to 87% ee were obtained. Based on X-ray crystallography and NMR studies, the origin of the observed enantioselectivities is discussed. KGaA.

Original language	English
Pages (from-to)	1412-1422
Number of pages	11
Journal	Advanced Synthesis and Catalysis
Volume	351
Issue number	9
DOIs	https://doi.org/10.1002/adsc.200900086
Publication status	Published - 1 Jun 2009

Keywords

Allylic alkylation
Asymmetric catalysis
Enantioselectivity
Ferrocenes
Phosphine-thioether ligands

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200900086

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title = "Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations",

abstract = "Chiral ferrocene-derived phosphine-thioether mixed donor ligands supported by heterocycles effected the palladium-catalyzed enantioselective allylic alkylations with excellent yields and enantioselectivities (up to 96% ee). With cyclic and unsymmetrical allylic acetates as substrate, the corresponding alkylated products with enantioselectivities up to 87% ee were obtained. Based on X-ray crystallography and NMR studies, the origin of the observed enantioselectivities is discussed. KGaA.",

keywords = "Allylic alkylation, Asymmetric catalysis, Enantioselectivity, Ferrocenes, Phosphine-thioether ligands",

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T1 - Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations

AU - Cheung, Hong Yee

AU - Yu, Wing Yiu

AU - Au-Yeung, Terry T.L.

AU - Zhou, Zhongyuan

AU - Chan, Albert S.C.

PY - 2009/6/1

Y1 - 2009/6/1

N2 - Chiral ferrocene-derived phosphine-thioether mixed donor ligands supported by heterocycles effected the palladium-catalyzed enantioselective allylic alkylations with excellent yields and enantioselectivities (up to 96% ee). With cyclic and unsymmetrical allylic acetates as substrate, the corresponding alkylated products with enantioselectivities up to 87% ee were obtained. Based on X-ray crystallography and NMR studies, the origin of the observed enantioselectivities is discussed. KGaA.

AB - Chiral ferrocene-derived phosphine-thioether mixed donor ligands supported by heterocycles effected the palladium-catalyzed enantioselective allylic alkylations with excellent yields and enantioselectivities (up to 96% ee). With cyclic and unsymmetrical allylic acetates as substrate, the corresponding alkylated products with enantioselectivities up to 87% ee were obtained. Based on X-ray crystallography and NMR studies, the origin of the observed enantioselectivities is discussed. KGaA.

KW - Allylic alkylation

KW - Asymmetric catalysis

KW - Enantioselectivity

KW - Ferrocenes

KW - Phosphine-thioether ligands

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DO - 10.1002/adsc.200900086

M3 - Journal article

SN - 1615-4150

VL - 351

SP - 1412

EP - 1422

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 9

ER -

Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations

Abstract

Keywords

ASJC Scopus subject areas

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