DOI: 10.1021/acs.joc.6c01458 ISSN: 0022-3263

Oxidative 1,2-Acyl Transfer for Nonspiro All-Carbon Quaternary Oxindoles Catalyzed by a Green System

Mengqi Wang, Jianfeng Wen, Wenli Liu, Tangmei Li, Jun Xu

Abstract

Developed herein is a green oxidative rearrangement strategy employing a KBr/oxone system that catalyzes 1,2-acyl transfer to access a diverse library of valuable 3,3-disubstituted nonspiro oxindoles bearing all-carbon quaternary centers. This approach exhibits exceptional functional group tolerance, accommodating esters, ketones, and amides, and is compatible with the late-stage functionalization of natural products. Additional features of this protocol include simple operation, facile purification, and broad scope, thus enabling the preparation of highly versatile building blocks susceptible to further modification.

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