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| - Regio- and Stereoselective Reactions of gem-DifluorinatedVinyloxiranes with Heteronucleophiles
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| - Regio- and stereoselectivity in reactions of gem-difluorinated vinyloxiranes with heteronucleophileswere successfully controlled. Halogen atoms were introduced regioselectively at the allylic epoxidecarbon with an inversion in stereochemistry using MgBr2·Et2O or Li2CuCl4 to produce anti-vic-halohydrine. The other diastereomers were obtained selectively using LiBr/AcOH or BCl3, and SN2‘type products were formed selectively with excellent E preference by changing the reactiontemperature. Moreover, a further investigation led us to find that a regio- and stereoselective SN2‘addition of several Brønsted acids was dependent on the pKa values of the acids. Under strongacidic conditions, we exclusively obtained E allylic alcohols.
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