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Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes.

ABSTRACT: A novel nickel-catalyzed asymmetric 1,2-vinylboration reaction has been developed to afford benzylic alkenylboration products with high yields and excellent enantioselectivities by using a chiral bisoxazoline ligand. Under optimized conditions, a wide variety of chiral 2-boryl-1,1-arylvinylalkanes are efficiently prepared from readily available olefins and vinyl halides in the presence of bis(pinacolato)diboron as the boron source in a mild and easy-to-operate manner. This three-component cascade protocol furnishes exceptional chemo- and stereoselectivity, and its usefulness is illustrated by its application in asymmetric modifications of several structurally complex natural products and pharmaceuticals.

SUBMITTER: Ye Y

PROVIDER: S-EPMC8513998 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes.

Ye Yang Y Liu Jiandong J Xu Bing B Jiang Songwei S Bai Renren R Li Shijun S Xie Tian T Ye Xiang-Yang XY

Chemical science 20210907 39

A novel nickel-catalyzed asymmetric 1,2-vinylboration reaction has been developed to afford benzylic alkenylboration products with high yields and excellent enantioselectivities by using a chiral bisoxazoline ligand. Under optimized conditions, a wide variety of chiral 2-boryl-1,1-arylvinylalkanes are efficiently prepared from readily available olefins and vinyl halides in the presence of bis(pinacolato)diboron as the boron source in a mild and easy-to-operate manner. This three-component cascad ...[more]

PMID: 34745552

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