Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines
ACS CatalysisPublished 13 September 2017
Fei Jiang, Dan Zhao, Xue Yang, Fu-Ru Yuan, Guang‐Jian Mei, Feng Shi
Citations114
SJR quartileQ1
SJR score3.78
SNIP2.03
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TL;DR
Catalyst-controlled chemoselective and enantioselectives reactions of tryptophols with isatin-derived imines were demonstrated, afforded 3-substituted 3-amino-oxindoles in generally good yields and excellent stereoselectivities.
Abstract
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).
Keywords
Chemistry
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