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

Published on 2018-12-06T14:50:11Z (GMT) by
A highly efficient asymmetric ring-opening/cyclopropanation reaction of (<i>E</i>)-3-(oxyethylidene)-2-oxoindolines with 1-alkyl-3-oxotetrahydro-1<i>H</i>-thiophen-1-ium salts as cyclic sulfur ylides was realized by using a chiral <i>N</i>,<i>N</i>′-dioxide/Mg­(OTf)<sub>2</sub> complex as catalyst. A range of sulfur-containing <i>syn</i>,<i>anti</i> 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.

Cite this collection

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.