Synthesis 2008(11): 1757-1760  
DOI: 10.1055/s-2008-1067041
© Georg Thieme Verlag Stuttgart · New York

A Convenient Route to Trifluoromethyl-Substituted Cyclopropane Derivatives

Pavel K. Mykhailiuka,c, Sergii Afoninb, Anne S. Ulrichb,c, Igor V. Komarov*a
a Kyiv National Taras Shevchenko University, 01033 Kyiv, Ukraine
b Institute of Biological Interfaces, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany
c Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany
Further Information

Publication History

Received 11 December 2007
Publication Date:
29 April 2008 (online)


A range of alkenes have been converted in a single step into the corresponding trifluoromethyl-substituted cyclopropanes by treatment with 2-diazo-l,l,l-trifluoroethane over metal catalysts. Application of the Gaspar-Roth procedure allowed the preparation of target compounds on a multi-gram scale. The practical utility of this reaction has been demonstrated by the synthesis of both diastereoisomers of the non-natural amino acid trifluoronorcoronamic acid in two steps.


Notably, Simonneaux and co-workers observed the stereoselective formation of only the trans-isomer 3a, while performing the trifluoromethyl-cyclopropanation of 3 over chiral metalloporphyrins (reference 9).