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

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...

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Bibliographic Details
Published in:Chinese journal of chemistry 2024-12, Vol.42 (23), p.3006-3012
Main Authors: Liu, Li‐Xia, Niu, Tong, Bai, Yu‐Qing, Zhou, Yong‐Gui
Format: Article
Language:English
Subjects:
Alkylation
Asymmetric allylic alkylation
Chemical synthesis
Chemoselectivity
Dynamic kinetic resolution
Lactones
Optical activity
Palladium
Palladium catalysis
Retro‐oxa‐Michael addition
Stereochemistry
Stereoselectivity
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Summary: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. 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.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202400612