Stereoselective Synthesis Of Trisubstituted (Z)-trifluoromethyl Alkenes

Abstract

A stereoselective synthesis of trisubstituted (Z)-trifluoromethyl alkenes has been developed. Treating allenes bearing a trifluoromethyl substituent with trifluoroacetic acid leads to the highly stereoselective formation of trisubstituted (Z)-trifluoromethyl alkenes. Treating trifluoromethyl allenes with Hg(OCOCF3)2 or iodine leads to fully substituted dienes. A novel synthesis of 3-trifluoromethyl-4-isoxazolines has developed. We demonstrated the synthesis of seven trifluoromethyl 4-isoxazolines, one heptafluoro-1-propyl 4-isoxazoline and one example of a non-fluorinated 4-isoxazoline.