Some special features of hydroalumination-iodination of alkyne-1,4-diols

Hydroalumination-iodination of alkyne-1,4-diols of different structure showed that with increasing number of substituents at the C-OH group the amount of β-iodo-substituted products with respect to this group increased. In the case of symmetric secondary 1,4-diols the reaction results in a 1: 1 mixture of stereoisomeric iodoalkenediols, and in the case of phenyl substituents the reaction proceeds regio- and stereoselectively to give an alkenediol iodine atom in the β-position to phenyl group.