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

Feng, Xiaoming

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

Posted on 2018-12-06 - 14:50

A highly efficient asymmetric ring-opening/cyclopropanation reaction of (E)-3-(oxyethylidene)-2-oxoindolines with 1-alkyl-3-oxotetrahydro-1H-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.

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Mei, Hongjiang; Pan, Guihua; Zhang, Xiying; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming (2018). Catalytic Asymmetric Ring-Opening/Cyclopropanation of Cyclic Sulfur Ylides: Construction of Sulfur-Containing Spirocyclopropyloxindoles with Three Vicinal Stereocenters. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b03187

https://doi.org/10.1021/acs.orglett.8b03187

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