Abstract
[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.
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