Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization

作者：Bing‐Nan Zhou, Qiuyue Wu, Ziyang Dong, Jiaxi Xu, Zhanhui Yang · 发表于：Organic Letters · 年份：2019 · DOI：10.1021/acs.orglett.9b01003 · 被引用次数：47 · 研究领域：Cyclopropane Reaction Mechanisms、Catalytic C–H Functionalization Methods、Synthesis and Catalytic Reactions

A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6- endo-trig/dig cyclization are realized, giving structurally diverse 4 H-thiopyran-4-ones and 2,3-dihydro-4 H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications of our formal (3 + 3) transannulations in the structural modifications of natural products.