884487-63-2Relevant academic research and scientific papers
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.
Divergent chemical synthesis of prolines bearing fluorinated one-carbon units at the 4-position via nucleophilic 5-endo-trig cyclizations
Nadano, Ryo,Iwai, Yu,Mori, Takashi,Ichikawa, Junji
, p. 8748 - 8754 (2007/10/03)
N-[3-(Trifluoromethyl)homoallyl]sulfonamides, prepared via ring opening of (5)-glycidyl ethers or 2-aryloxiranes with 1-(trifluoromethyl)vinyllithium, underwent intramolecular addition or SN2′-type reaction in the normally disfavored 5-endo-tri
