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Paper | Regular issue | Vol 94, No. 5, 2017, pp.879-893
Published online, 27th April, 2017
DOI: 10.3987/COM-17-13677
Highly Efficient Construction of CF3-Containing 3,3’-Pyrrolidinyl-dispirooxindoles via Base-Catalyzed Diastereoselective [3+2] Annulation

Wei-Jie Huang, Qing Chen, Wen-Run Zhu, Ning Lin,* Xian-Wen Long, Wei-Gao Pan, Jiang Weng,* and Gui Lu

*Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

Abstract

An efficient base-catalyzed diastereoselective [3+2] cyclization of isatin-derived azomethine ylides with methyleneindolinones was developed. The process enables efficient incorporation of CF3 groups into highly functionalized 3,3’-pyrrolidinyl-dispirooxindoles bearing four contiguous chiral centers, including two adjacent spiro quaternary stereocenters, with high yields and diastereoselectivities.