An Efficient Substrate-Induced Method for the Synthesis of CF3-Substituted Cyclopropanes by Metal-Free Reaction of Trifluoromethyl Styrylisoxazoles with Nitromethane

A series of (trifluoromethyl)cyclopropanes (TFCPs) tolerating a broad range of functional groups, known as tert-butyl bioisosteres, have been obtained from the cyclization reaction between nitromethane- and 5-[beta-(trifluoromethyl)styryl]isoxazoles in 70-94% yields and 75:25 to 90:10 dr. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing an inorganic base under phase-transfer conditions.

Automated summary

A series of (trifluoromethyl)cyclopropanes have been synthesized in high yields through the cyclization reaction between nitromethane and 5-[beta-(trifluoromethyl)styryl]isoxazoles. This method, which employs an inorganic base under phase-transfer conditions, provides a practical approach for accessing the cyclopropyl moiety of pharmacological interest.