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

Li-Xia Liu; Tong Niu; Yu-Qing Bai; Yong-Gui Zhou

doi:10.1002/cjoc.202400612

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (23) : 3006 -3012. DOI: 10.1002/cjoc.202400612

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

Li-Xia Liu ¹^,²
, Tong Niu ¹
, Yu-Qing Bai ¹
, Yong-Gui Zhou ¹^,³^,^†

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Abstract

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.

Keywords

Retro-oxa-Michael addition / Dynamic kinetic resolution / Palladium catalysis / Asymmetric allylic alkylation / Chemoselectivity / Stereochemistry / Lactones

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Li-Xia Liu, Tong Niu, Yu-Qing Bai, Yong-Gui Zhou. Palladium-Catalyzed Construction of Phthalides Bearing Two Adjacent Stereocenters through Retro-oxa-Michael Addition. Chinese Journal of Chemistry, 2024, 42(23): 3006-3012 DOI:10.1002/cjoc.202400612