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Chiral Bicyclic Guanidine-Catalyzed Enantioselective Sulfenylation of Oxindoles and Benzofuran-2(3H)‑ones
journal contribution
posted on 2015-09-04, 00:00 authored by Lisha Huang, Jiangtao Li, Yan Zhao, Xinyi Ye, Yang Liu, Lin Yan, Choon-Hong Tan, Hongjun Liu, Zhiyong JiangA 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).