A highly regio- and chemoselective synthesis of vicinal bromohydrins by ring opening of terminal epoxides with dibromoborane-dimethyl sulfide

Article abstract of DOI:10.1016/j.jorganchem.2006.11.032

Dibromoborane-dimethyl sulfide (BHBr₂-SMe₂) displays high degrees of chemo- and regioselectivity during the brominative cleavage of the epoxy group into vicinal bromohydrins in the presence of alkene, alkyne, allene, ether, acetal and acetonide, besides its hydroborating ability. Several reducible functional groups, such as chloride, aldehyde, ketone, azide, ester, nitrile and tert-amino ester, have been successfully accommodated during the epoxide opening process.