NUCLEOPHILIC CLEAVAGES OF ACETALS USING ORGANOTITANIUM REAGENTS. A NEW SYNTHESIS OF CHIRAL ALCOHOLS

Article abstract of DOI:10.1016/S0040-4039(01)81455-6

A highly chemo- and stereoselective cleavage of acetals derived from (-)-(2R, 4R)-2,4-pentanediol with organotitanium reagents has been demonstrated.The reraction proceeds under mild condations in excellent yield and high chemoselectivity to give, after removel of auxiliary, the chiral alcohols of high enantiopurities.In addition, complexation of chiral acetals and TiCl4 followed by treatment with n-butyllithium also results in formation of the corresponding n-butylated alcohols with high stereoselectivity.