Jump to main content
Jump to site search


Solvent-Free, Uncatalyzed Asymmetric “Ene” Reactions of N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimines: General Approach to Enantiomerically Pure alfa-(Trifluoromethyl)tryptamines.

Abstract

A novel approach to regioselectively substituted and stereoselectively -trifluoromethylated tryptamines is reported based on the ene reaction of Boc-protected 3-methyleneindolines with optically pure (R)- or (S)-tert-butanesulfinyltrifluoroacetaldimine. Boc- and sulfinylamido-protected -trifluoromethyltryptamines are obtained in 60-70% yield and 85/15 dr by just heating equimolar amounts of the two reaction partners at 80–90 °C for 2-3 h without solvent. The absolute configuration of the amino -carbon has been assigned based on the vibrational circular dichroim (VCD) spectral analysis. The two protecting group can be chemoselectively removed allowing further regio- and stereoselective elaboration of the ene products to various biologically interesting compounds.

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 18 Mar 2017, accepted on 12 Apr 2017 and first published on 12 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00670E
Citation: Org. Biomol. Chem., 2017, Accepted Manuscript
  •   Request permissions

    Solvent-Free, Uncatalyzed Asymmetric “Ene” Reactions of N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimines: General Approach to Enantiomerically Pure alfa-(Trifluoromethyl)tryptamines.

    R. Ruzziconi, G. Mazzeo, G. Longhi, S. Abbate, M. Palomba, L. Bagnoli, F. Marini, C. Santi, J. Han, V. A. Soloshonok and E. Di Crescenzo, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB00670E

Search articles by author