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Reaction of gem-difluorinated vinyloxiranes with RCu(X)Li allowed us to introduce the R group regioselectively at the fluorine-attached terminal carbon atom in an S N 2′ manner to afford (E)-allylic alcohols exclusively, while homoallylic alcohols with anti stereochemical relationship were found to be obtained selectively from higher-ordered cuprates derived from CuCl and RMgBr in a ratio...
gem-Difluorinated vinyloxiranes, which are useful synthetic intermediates for difluorinated compounds, were brominated regio- and stereoselectively. Introduction of bromide at the allylic epoxide carbon with inversion of stereochemistry was realized by MgBr 2 ·Et 2 O to furnish an anti vic-bromohydrine, whereas the reaction with LiBr/AcOH afforded the other diastereomer selectively...
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