ENANTIOSELECTIVE SYNTHESIS OF 2-BENZYLOXY ALCOHOLS AND 1,2-DIOLS VIA ALKYLATION OF CHIRAL GLYCOLATE IMIDES. A CONVENIENT APPROACH TO OPTICALLY ACTIVE GLYCEROL DERIVATIVES

Article abstract of DOI:10.1016/0040-4020(89)80148-6

The alkylation of the chiral enolates of glycolate imides 2a and 2b proceedes in highly diastereoselective manner to give 2'-substituted products in good yield.Reductive cleavage with LiBH4 affords the corresponding 2-benzyloxyalcohols 3a-c and 11a-b which are successively converted to 1,2-diols in high optical purity.By this method (R)-1-propanoyloxy-2,3-propanediol 9 and (S)-1-tridecyloxy-2,3-propanediol 14, a glyceride extracted from sponges Plocamiidae, have been synthesized, starting from 2a and 2b, respectively.