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Issue 46, 2013
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Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine

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Abstract

Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine were found to proceed with reasonably good yields (55%–79%) and exceptionally high stereoselectivity (>99 : 1 dr). This method presents a general approach for the preparation of a new type of biologically relevant compounds containing pharmacophoric imidazo[2,1-b]thiazole and (trifluoro)ethylamine groups.

Graphical abstract: Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine

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Publication details

The article was received on 02 Sep 2013, accepted on 17 Oct 2013 and first published on 17 Oct 2013


Article type: Communication
DOI: 10.1039/C3OB41785A
Citation: Org. Biomol. Chem., 2013,11, 8018-8021
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    Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine

    H. Mei, C. Xie, L. Wu, V. A. Soloshonok, J. Han and Y. Pan, Org. Biomol. Chem., 2013, 11, 8018
    DOI: 10.1039/C3OB41785A

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