Issue 20, 2011
From the journal:

Organic & Biomolecular Chemistry

Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

Sara Kenis,a   Matthias D'hooghe,*a   Guido Verniest,†a   Vinh Duc Nguyen,b   Tuyet Anh Dang Thi,b   Tuyen Van Nguyenb  and  Norbert De Kimpe*a  

* Corresponding authors

a Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent, Belgium
E-mail: norbert.dekimpe@UGent.be, matthias.dhooghe@UGent.be

b Institute of Chemistry, Vietnam Academy of Science & Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam

Abstract

An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetoneviaimination, α-chlorination, hydride reduction and ring closure was developed. In addition, novel primary β-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel α-CF3-β-phenylethylamines upon treatment with lithium diphenylcuprate.

Graphical abstract: Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

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Article information

DOI
https://doi.org/10.1039/C1OB05813D
Article type
Paper
Submitted
24 May 2011
Accepted
17 Jun 2011
First published
17 Jun 2011

Org. Biomol. Chem., 2011,9, 7217-7223

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Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

S. Kenis, M. D'hooghe, G. Verniest, V. D. Nguyen, T. A. D. Thi, T. V. Nguyen and N. D. Kimpe, Org. Biomol. Chem., 2011, 9, 7217 DOI: 10.1039/C1OB05813D

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