Chiral Bicyclic Guanidine-Catalyzed Enantioselective Sulfenylation of

Oxindoles and Benzofuran-2(3H)-ones

Lisha Huang, Jiangtao Li, Yan Zhao, Xinyi Ye, Yang Liu, Lin Yan, Choon-Hong Tan, Hongjun Liu and Zhiyong Jiang

J. Org. Chem.201580178933-8941

Abstract: A chiral bicyclic guanidine-catalyzed enantioselective sulfenylation of 3-substituted oxindoles to N-(sulfanyl)succinimides has been developed. A series of unprecedented 3-sulfenylated oxindoles, such as 3-benzyl/alkyl-substituted 3-benzyl/alkyloxindoles, were obtained with high enantioselectivities (up to 98% ee). This methodology is also effective for the first asymmetric sulfenylation of benzofuran-2(3H)-ones, providing 3-benzyl-3-benzylthio-substituted benzofuran-2(3H)-ones with satisfactory results (up to 95% ee).

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