Dimethoxyboron bromide – a new,efficient,regio- and chemoselective reagent for the conversion of terminal epoxides into bromohydrins

Abstract

Dimethoxyboron bromide, (MeO)₂BBr, easily prepared in excellent yield from boron tribromide and trimethyl borate, is a new, efficient, regio- and chemoselective reagent useful for the halogenative cleavage of compounds containing epoxy groups into vicinal bromohydrins in the presence of ether, acetal, ketal, N-oxide, and sulfoxide groups, at low temperatures (–78°C).

Keywords

dimethoxyboron bromide epoxide bromohydrin regioselectivity chemoselectivity

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