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Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C-H activation.

ABSTRACT: A novel method by a one-step introduction of axial chirality and sterically hindered group has been developed for facile synthesis of axially chiral styrene-type carboxylic acids. With the palladium-catalyzed C-H arylation and olefination of readily available cinnamic acid established, this transformation demonstrated excellent yield, excellent stereocontrol (up to 99% yield and 99% ee), and broad substrate scope under mild conditions. The axially chiral styrene-type carboxylic acids produced have been successfully applied to Cp*Co^III-catalyzed asymmetric C-H activation reactions, indicating their potential as chiral ligands or catalysts in asymmetric synthesis.

SUBMITTER: Yang C

PROVIDER: S-EPMC8179534 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Facile synthesis of axially chiral styrene-type carboxylic acids <i>via</i> palladium-catalyzed asymmetric C-H activation.

Yang Chi C Wu Tian-Rui TR Li Yan Y Wu Bing-Bing BB Jin Ruo-Xing RX Hu Duo-Duo DD Li Yuan-Bo YB Bian Kang-Jie KJ Wang Xi-Sheng XS

Chemical science 20210120 10

A novel method by a one-step introduction of axial chirality and sterically hindered group has been developed for facile synthesis of axially chiral styrene-type carboxylic acids. With the palladium-catalyzed C-H arylation and olefination of readily available cinnamic acid established, this transformation demonstrated excellent yield, excellent stereocontrol (up to 99% yield and 99% ee), and broad substrate scope under mild conditions. The axially chiral styrene-type carboxylic acids produced ha ...[more]

PMID: 34163646

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