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Synthesis 2013; 45(2): 225-230
DOI: 10.1055/s-0032-1316831
DOI: 10.1055/s-0032-1316831
paper
Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine
Further Information
Publication History
Received: 02 November 2012
Accepted after revision: 29 November 2012
Publication Date:
18 December 2012 (online)
Abstract
Two isomeric conformationally restricted analogues of 4-trifluoromethylpiperidine were designed. The synthesis was performed in four steps from commercially available N-benzylmaleimide. The key reaction was the [3+2] cycloaddition between trifluoromethyldiazomethane and N-benzylmaleimide.
Key words
amines - trifluoromethyl group - cyclopropane - 4-trifluoromethylpiperidine - drug designSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are copies of NMR spectra and crystallographic data for compounds 12a and 14.
- Supporting Information
-
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For some recent examples, see:
For some recent reviews on this topic, see:
Some recent papers:
Selected papers on trifluoromethylcyclopropanes:
For trifluoromethylcyclopropanes obtained by metal-catalyzed trifluoromethylcyclopropanation of alkenes by CF3CHN2, see: