Stereospecific and regiospecific ring opening of glycidol with primary and secondary alcohols mediated by diisobutylaluminium hydride

Regiospecific ring opening of (R)-(+)- or (S)-(–)-glycidol 1a, b with primary and secondary alcohols in the presence of diisobutylaluminium hydride provides 1-O-alkyl-sn-glycerol 2 without formation of the undesired regioisomer, 2-O-alkylglycerol 3. The configuration of the glycidol is preserved in the product.