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

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 transfor...

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Veröffentlicht in:Chemical science (Cambridge) 2021-01, Vol.12 (10), p.3726-3732
Hauptverfasser: Yang, Chi, Wu, Tian-Rui, Li, Yan, Wu, Bing-Bing, Jin, Ruo-Xing, Hu, Duo-Duo, Li, Yuan-Bo, Bian, Kang-Jie, Wang, Xi-Sheng
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Sprache:eng
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Zusammenfassung: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc06661c