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

An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, α-chlorination, hydride reduction and ring closure was developed. In addition, novel primary β-iodo amines were obtained by regioselective ring...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2011-10, Vol.9 (20), p.7217-7223
Main Authors: Kenis, Sara, D'hooghe, Matthias, Verniest, Guido, Nguyen, Vinh Duc, Thi, Tuyet Anh Dang, Nguyen, Tuyen Van, De Kimpe, Norbert
Format: Article
Language:English
Subjects:
Acetone - analogs & derivatives
Acetone - chemistry
Alkylation
Aziridines - chemical synthesis
Fluorine Compounds - chemical synthesis
Methylation
Molecular Structure
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Summary:An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, 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-CF(3)-β-phenylethylamines upon treatment with lithium diphenylcuprate.
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob05813d