Regio- and stereoselective reductions of gem-difluorinated vinyloxiranes.
[reaction: see text] gem-Difluorinated vinyloxiranes are versatile building blocks for the synthesis of fluorinated compounds. Investigations of their reactions with nucleophiles resulted in highly regio- and stereoselective reductions. In their reactions with LiAlH4, hydride reacted at the allylic epoxide carbon to produce homoallylic alcohols exclusively. Moreover, regio- and stereoselective S(N)2' reactions were observed with DIBAL-H and BH3 x THF; the former afforded E allylic alcohols, whereas the latter furnished the corresponding Z isomers with excellent selectivities.
Ueki
Hisanori
H
Graduated School of Bioscience and Bioengineering, Tokyo Institute of Technology, 4259 Nagatuta-cho, Midori-ku, Yokohama 226-8501, Japan.
Chiba
Takashi
T
Kitazume
Tomoya
T