3 years ago

Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines

Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines
Feng Shi, Fu-Ru Yuan, Xue Yang, Guang-Jian Mei, Fei Jiang, Dan Zhao
Catalyst-controlled chemoselective and enantioselective reactions of tryptophols with isatin-derived imines were demonstrated. Under catalysis with a chiral phosphoric acid, diastereoselective and enantioselective dearomative cyclization occurred, while, in the presence of a chiral squaramide-tertiary amine, enantioselective addition occurred. Both reactions afforded 3-substituted 3-amino-oxindoles in generally good yields (up to 99%) and excellent stereoselectivities (up to >95:5 dr, 99:1 er).

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02279

DOI: 10.1021/acscatal.7b02279

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