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Issue 13, 2014
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Concise and scalable asymmetric synthesis of 5-(1-amino-2,2,2-trifluoroethyl)thiazolo[3,2-b][1,2,4]triazoles

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Abstract

This study describes asymmetric Mannich-type additions between C-5 lithiated thiazolo[3,2-b][1,2,4]triazoles and enantiomerically pure (SS)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine. Under the optimized conditions, these reactions proceed with good (up to 78%) chemical yields and virtually complete (98 : 2 to >99 : 1 dr) diastereoselectivity. The same stereochemical outcome was obtained using 1.05 g scale of the starting (3,3,3)-trifluoroacetaldimine. The method developed in this work provides concise and generalized access to thiazolo[3,2-b][1,2,4]triazoles containing a chiral (trifluoro)ethylamine group.

Graphical abstract: Concise and scalable asymmetric synthesis of 5-(1-amino-2,2,2-trifluoroethyl)thiazolo[3,2-b][1,2,4]triazoles

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Publication details

The article was received on 24 Nov 2013, accepted on 29 Jan 2014 and first published on 29 Jan 2014


Article type: Paper
DOI: 10.1039/C3OB42348D
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 2108-2113
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    Concise and scalable asymmetric synthesis of 5-(1-amino-2,2,2-trifluoroethyl)thiazolo[3,2-b][1,2,4]triazoles

    H. Mei, Y. Xiong, C. Xie, V. A. Soloshonok, J. Han and Y. Pan, Org. Biomol. Chem., 2014, 12, 2108
    DOI: 10.1039/C3OB42348D

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