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

Author:
Zhou, Bingnan, Wu, Qiuyue, Dong, Ziyang, Xu, Jiaxi, Yang, Zhanhui
Source:
Organic letters 2019 v.21 no.10 pp. 3594-3599
ISSN:
1523-7052
Subject:
aldehydes, carbenes, chemical reactions, chemical structure
Abstract:
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 4H-thiopyran-4-ones and 2,3-dihydro-4H-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.
Agid:
6445831