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Asymmetric Synthesis of (3S,1'S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one Derivatives by Addition of (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to 1-(alkyl)-indolin-2-ones

Asymmetric Synthesis of (3S,1'S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one Derivatives by Addition of (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to 1-(alkyl)-indolin-2-ones

Ping Qian, Chen Xie, Lingmin Wu, Haibo Mei, Vadim A Soloshonok, Jianlin Han, Yi Pan

Org Biomol Chem. 2014 Oct 28;12(40):7909-13.

PMID: 25220306

Abstract:

This paper presents the first study of the addition reactions between amide-derived nucleophiles and chiral CF3-containing N-sulfinyl-imines. We demonstrate that enolates of 1-(alkyl)-indolin-2-ones cleanly react with (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine affording 3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-ones of (3S,1'S) absolute configuration as the major reaction products with synthetically meaningful diastereoselectivity and chemical yields. The reactions were shown to be of general practical application for preparation of various oxindole derivatives in a diastereomerically pure form.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP22753806	2-[N-(2,2,2-Trifluoroethyl)amino]-5-chlorobenzophenone		22753-80-6	Price

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