Bromolysis and iodolysis of alpha,beta-epoxycarboxylic acids in water catalyzed by indium halides

The ring opening of alpha,beta -epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereose lective fashion. The iodolysis of trans-beta -monoalkylated epoxycarboxylic acids at pH 4.0 was completely ol-regioselective and anti diastereoselecti ve. The InCl3-catalyzed iodolysis of a variety of alpha,beta -epoxycarboxyl ic acids at pH 1.5 gave the corresponding anti beta -iodohydrins in 88-95% yields. The one-pot synthesis of the alpha- and beta -hydroxyhexanoic acids , starting from the corresponding alpha,beta -epoxycarboxylic acid 1a by io dolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaB H4-InCl3 in water, has been performed.