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

Abstract

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-[β-(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.

Key words

styrylisoxazole - cyclization - trifluoromethyl - cyclopropane - inorganic base - phase-transfer catalyst

Publikationsverlauf

Eingereicht: 02. Oktober 2020

Angenommen nach Revision: 21. Oktober 2020

Artikel online veröffentlicht:
19. November 2020

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