A method for syn-dihydroxylation of double bonds cis to a hydroxymethyl substituent

Results show that the carboxymethylation of a homoallylic alcohol occurs via iodolactonization mediated by iodonium dicollidine hexafluorophosphate. The substitution of the iodide with silver trifluoroacetate instead of chloroacetic acid results in the diastereoselective syn-syn dihydroxylation of the double bond in cyclic alkene and possibly with the cyclic allylic alcohols as well.