Efficient synthesis of functionalized trifluoromethyl cyclopropanes via cyclopropanation of & alpha;-trifluoromethyl styrenes with chloroacetonitrile and ethyl chloroacetate

An efficient and practical method for the synthesis of functionalized trifluoromethyl cyclopropanes via cyclopropanation of & alpha;-trifluoromethyl styrenes with chloroacetonitrile or ethyl chloroacetate was developed. In some cases, the mixture of trans- and cis-isomers could be separated by column chromatography. The configurations of the trans-/cis-isomers were further confirmed by heteronuclear H-1-F-19 NOESY experiments.

Automated summary

An efficient and practical method was developed for synthesizing functionalized trifluoromethyl cyclopropanes through cyclopropanation of α-trifluoromethyl styrenes with chloroacetonitrile or ethyl chloroacetate. In some cases, the trans- and cis-isomers could be separated by column chromatography. The configurations of the trans-/cis-isomers were further confirmed by heteronuclear H-1-F-19 NOESY experiments.