Iodohydroxylation of alkenes promoted by molecular and hypervalent(III) iodine

Several iodohydrins are isolated in good yields starting from the corresponding alkenes and a mixture of molecular iodine and phenyliodine(III)bis(trifluoroacetate) (BTI), in CH3CN–H2O as solvent, at −15°C. Hypoiodous acid is added to the terminal carboncarbon double bond in a Markovnikov fashion. Moreover, the stereochemical features of the products show the anti-stereospecificity of the addition.