Abstract
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•Regioselective and stereocontrolled vinyl epoxide opening.•Regioselective and stereocontrolled vinyl aziridine opening.•Efficient formation of vicinal halohydrins and haloamines.
A new metal-free method is reported for the stereocontrolled opening of vinyl epoxides using boron trichloride or tribromide to yield the corresponding vicinal chlorohydrins and bromohydrins with high regioselectivities and exclusive diastereoselectivity. Synthesis of vicinal haloamines from vinyl aziridines was also demonstrated under the same conditions.