Chemoselective 1-ethylpiperidine hypophosphite (EPHP)-mediated intermolecular radical additions of 1-deoxy-1-halo-1-iodo-alditols to electron-deficient olefins

The chemoselective radical reduction of the iodine atom in a series of 1-deoxy-1-halo-1-iodo-alditols with the 1-ethylpiperidine hypophosphite (EPHP)/AIBN system is described. EPHP is also a good chain carrier for the radical addition of gem-dihalocompounds to electron-deficient olefins. Thus, the synthesis of 4-halo-glycooctononitriles and 4-halo-glycoheptononitriles can be achieved by an intermolecular addition of the 1-deoxy-1-halo-alditol-1-yl radical intermediate to acrylonitrile.