884487-63-2Relevant articles and documents
1-(Trifluoromethyl)vinylation via oxirane or oxetane ring-opening: A facile synthesis of 4- or 5-hydroxy-functionalized 2-trifluoromethyl-1-alkenes
Nadano, Ryo,Ichikawa, Junji
, p. 128 - 132 (2006)
Introduction of a 1-(trifluoromethyl)vinyl group has been accomplished by the reaction of thermally unstable 1-(trifluoromethyl)vinyllithium (1) with strained cyclic ethers. Treatment of 2-bromo-3,3,3-trifluoropropene with butyllithium generates 1, which in turn reacts with several oxiranes or an oxetane at -100 °C in the presence of BF3·OEt2 to afford the corresponding 2-trifluoromethyl-1-alkenes bearing a hydroxy group on the 4- or 5-position. An enantiopure oxirane undergoes ring-opening without racemization, providing an optically active homoallyllic alcohol with a 3-trifluoromethyl group. Georg Thieme Verlag Stuttgart.