Volume 42, Issue 23 pp. 3006-3012
Concise Report

Palladium-Catalyzed Construction of Phthalides Bearing Two Adjacent Stereocenters through Retro-oxa-Michael Addition

Li-Xia Liu

Li-Xia Liu

State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China

University of Chinese Academy of Sciences, Beijing, 100049 China

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Tong Niu

Tong Niu

State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China

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Yu-Qing Bai

Yu-Qing Bai

State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China

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Yong-Gui Zhou

Corresponding Author

Yong-Gui Zhou

State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China

E-mail: [email protected]Search for more papers by this author
First published: 21 August 2024

Comprehensive Summary

Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium-catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo-, enantio- and diastereoselectivity. Furthermore, gram-scale experiment underwent smoothly and the transformation of product could build a bridged bicyclic skeleton.

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