A Convenient Route to Trifluoromethyl-Substituted Cyclopropane Derivatives

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

References

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11

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).