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

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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

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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, Advance Article
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    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, Advance Article , DOI: 10.1039/C7OB00670E

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