Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand

Hao Wang; Zibo Bai; Tangqian Jiao; Zhiqiang Deng; Huarong Tong; Gang He; Qian Peng; Gong Chen

doi:10.1021/jacs.8b00641

Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand

Hao Wang, Zibo Bai, Tangqian Jiao, Zhiqiang Deng, Huarong Tong, Gang He, Qian Peng, Gong Chen

Chemistry

Research output: Contribution to journal › Article › peer-review

128 Scopus citations

Abstract

A Pd-catalyzed amide-directed enantioselective hydrocarbofunctionalization of unactivated alkenes with C-H nucleophiles has been developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.

Original language	English (US)
Pages (from-to)	3542-3546
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	10
DOIs	https://doi.org/10.1021/jacs.8b00641
State	Published - Mar 14 2018

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.8b00641

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abstract = "A Pd-catalyzed amide-directed enantioselective hydrocarbofunctionalization of unactivated alkenes with C-H nucleophiles has been developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.",

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AU - Wang, Hao

AU - Bai, Zibo

AU - Jiao, Tangqian

AU - Deng, Zhiqiang

AU - Tong, Huarong

AU - He, Gang

AU - Peng, Qian

AU - Chen, Gong

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Y1 - 2018/3/14

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AB - A Pd-catalyzed amide-directed enantioselective hydrocarbofunctionalization of unactivated alkenes with C-H nucleophiles has been developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.

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Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand

Abstract

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