Issue 40, 2014

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

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Communication
Submitted
10 Jul 2014
Accepted
02 Sep 2014
First published
02 Sep 2014

Org. Biomol. Chem., 2014,12, 7909-7913

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

P. Qian, C. Xie, L. Wu, H. Mei, V. A. Soloshonok, J. Han and Y. Pan, Org. Biomol. Chem., 2014, 12, 7909 DOI: 10.1039/C4OB01453G

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