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Asymmetric β-arylation of cyclopropanols enabled by photoredox and nickel dual catalysis.

ABSTRACT: The enantioselective functionalization and transformation of readily available cyclopropyl compounds are synthetically appealing yet challenging topics in organic synthesis. Here we report an asymmetric β-arylation of cyclopropanols with aryl bromides enabled by photoredox and nickel dual catalysis. This dual catalytic transformation features a broad substrate scope and good functional group tolerance at room temperature, providing facile access to a wide array of enantioenriched β-aryl ketones bearing a primary alcohol moiety in good yields with satisfactory enantioselectivities (39 examples, up to 83% yield and 90% ee). The synthetic value of this protocol was illustrated by the concise asymmetric construction of natural product calyxolane B analogues.

SUBMITTER: Wang J

PROVIDER: S-EPMC8905987 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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Asymmetric β-arylation of cyclopropanols enabled by photoredox and nickel dual catalysis.

Wang Jianhua J Li Xiaoxun X

Chemical science 20220217 10

The enantioselective functionalization and transformation of readily available cyclopropyl compounds are synthetically appealing yet challenging topics in organic synthesis. Here we report an asymmetric β-arylation of cyclopropanols with aryl bromides enabled by photoredox and nickel dual catalysis. This dual catalytic transformation features a broad substrate scope and good functional group tolerance at room temperature, providing facile access to a wide array of enantioenriched β-aryl ketones ...[more]

PMID: 35382467

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