Issue 18, 2017

Solvent-free, uncatalyzed asymmetric “ene” reactions of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines: a general approach to enantiomerically pure α-(trifluoromethyl)tryptamines

Abstract

A novel approach to regioselectively substituted and stereoselectively α-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 α-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 a solvent. The absolute configuration of the amino α-carbon has been assigned based on the vibrational circular dichroism (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.

Graphical abstract: Solvent-free, uncatalyzed asymmetric “ene” reactions of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines: a general approach to enantiomerically pure α-(trifluoromethyl)tryptamines

Supplementary files

Article information

Article type
Paper
Submitted
18 Mar 2017
Accepted
12 Apr 2017
First published
12 Apr 2017

Org. Biomol. Chem., 2017,15, 3930-3937

Solvent-free, uncatalyzed asymmetric “ene” reactions of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines: a general approach to enantiomerically pure α-(trifluoromethyl)tryptamines

G. Mazzeo, G. Longhi, S. Abbate, M. Palomba, L. Bagnoli, F. Marini, C. Santi, J. Han, V. A. Soloshonok, E. Di Crescenzo and R. Ruzziconi, Org. Biomol. Chem., 2017, 15, 3930 DOI: 10.1039/C7OB00670E

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