Asymmetric Friedel-Crafts reactions of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines: general access to enantiomerically pure indoles containing a 1-amino-2,2,2-trifluoroethyl group

Lingmin Wu; Chen Xie; Haibo Mei; Vadim A Soloshonok; Jianlin Han; Yi Pan

doi:10.1021/jo5012009

Asymmetric Friedel-Crafts reactions of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines: general access to enantiomerically pure indoles containing a 1-amino-2,2,2-trifluoroethyl group

J Org Chem. 2014 Aug 15;79(16):7677-81. doi: 10.1021/jo5012009. Epub 2014 Jul 28.

Authors

Lingmin Wu¹, Chen Xie, Haibo Mei, Vadim A Soloshonok, Jianlin Han, Yi Pan

Affiliation

¹ School of Chemistry and Chemical Engineering, Nanjing University , Nanjing 210093, China.

PMID: 25051149
DOI: 10.1021/jo5012009

Abstract

We have demonstrated that 3,3,3-trifluoroacetaldimine (S)-1 easily reacts with indole derivatives under Friedel-Crafts reactions to provide reliable and generalized access to biologically interesting compounds containing the CF3CH(NH2)- pharmacophoric group. The reactions proceed with high rates and generally excellent yields (>90%) and stereochemical outcomes (99:1 dr).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrocarbons, Fluorinated / chemistry*
Indoles / chemistry*
Molecular Structure
Stereoisomerism
Sulfonium Compounds / chemistry*

Substances

(S)-N-(tert-butanesulfinyl)-3,3,3-trifluoroacetaldimine
Hydrocarbons, Fluorinated
Indoles
Sulfonium Compounds