Reaction of (Z)-1-bromoalk-1-enyldialkylboranes with DMSO: regio- and stereo-selective formation of internal (E)-alkenyl bromides

Abstract

Treatment of (Z)-1-bromoalk-1-enyldialkylboranes 1 with DMSO results in 1,2-migration of an alkyl group from the boron to the α-carbon without elimination of bromine to give internal (E)-alkenyl bromides 2 with excellent stereoselectivity (>99%).

References

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