Chiral Bicyclic Guanidine-Catalyzed Enantioselective Sulfenylation of Oxindoles and Benzofuran-2(3H)-ones

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• 作者：Lisha Huang ; Jiangtao Li ; Yan Zhao ; Xinyi Ye ; Yang Liu ; Lin Yan ; Choon-Hong Tan ; Hongjun Liu ; Zhiyong Jiang
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：September 4, 2015
• 年：2015
• 卷：80
• 期：17
• 页码：8933-8941
• 全文大小：461K
• ISSN：1520-6904

文摘

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).