Regio- and stereoselective reductions of gem-difluorinated vinyloxiranes

作者：Ueki H^*; Chiba T; Kitazume T

来源：Organic Letters, 2005, 7(7): 1367-1370.

DOI：10.1021/ol050173z

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 BH(3)center dot THF; the former afforded E allylic alcohols, whereas the latter furnished the corresponding Z isomers with excellent selectivities.

• 出版日期2005-3-31