Catalytic Asymmetric Ring-Opening/Cyclopropanation of Cyclic Sulfur Ylides: Construction of Sulfur-Containing Spirocyclopropyloxindoles with Three Vicinal Stereocenters

作者：Hongjiang Mei, Guihua Pan, Xiying Zhang, Lili Lin, Xiaohua Liu, Xiaoming Feng · 发表于：Organic Letters · 年份：2018 · DOI：10.1021/acs.orglett.8b03187 · 被引用次数：36 · 研究领域：Cyclopropane Reaction Mechanisms、Sulfur-Based Synthesis Techniques、Asymmetric Synthesis and Catalysis

A highly efficient asymmetric ring-opening/cyclopropanation reaction of ( E )-3-(oxyethylidene)-2-oxoindolines with 1-alkyl-3-oxotetrahydro-1 H -thiophen-1-ium salts as cyclic sulfur ylides was realized by using a chiral N, N ′-dioxide/Mg(OTf) 2 complex as catalyst. A range of sulfur-containing syn, anti spirocyclopropyloxindoles with three contiguous stereocenters were obtained in excellent yields with excellent dr and good ee values under mild reaction conditions. The origin of stereoselectivity was discussed.