STUDY OF THE CONDITIONS OF THE RUTHENIUM TETRAOXIDE-PROMOTED OXIDATIVE CLEAVAGE REACTION OF BICYCLIC beta-HYDROXY ETHERS

摘要

STUDY OF THE CONDITIONS OF THE RUTHENIUM TETRAOXIDE-PROMOTED OXIDATIVE CLEAVAGE REACTION OF BICYCLIC P-HYDROXY ETHERS. A systematic study of the reaction of beta-hydroxy ethers with ruthenium tetraoxide (RuO4), generated in situ from ruthenium trichloride and sodium periodate, is presented, leading to nine-membered ring keto-lactones in moderate yields. Three different solvent systems - AcOEt/MeCN/H2O, MeCN/H2O and DMC/H2O - were studied leading to the desired products in lower yields than those obtained with the classical mixture of CCl4/MeCN/H2O, commonly used in reactions promoted by this oxidant. However, it is noteworthy that these new solvent systems represent greener alternatives to the chlorinated solvents used in the oxidative cleavage of beta-hydroxy ethers by RuO4.