A Convenient Route to Trifluoromethyl-Substituted Cyclopropane Derivatives

Pavel K. Mykhailiuk; Sergii Afonin; Anne S. Ulrich; Igor V. Komarov

doi:10.1055/s-2008-1067041

PAPER

A Convenient Route to Trifluoromethyl-Substituted Cyclopropane Derivatives

Pavel K. Mykhailiuk^a,c, Sergii Afonin^b, Anne S. Ulrich^b,c, Igor V. Komarov*^a
^a Kyiv National Taras Shevchenko University, 01033 Kyiv, Ukraine
e-Mail: ik214@yahoo.com;
^b Institute of Biological Interfaces, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany
^c Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany

Abstract

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Abstract

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.

Key words

fluorine - alkenes - amino acids - catalysts - diazo compounds

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Referenzen

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