One-pot generation and conversion of trichloroacetimidates for the racemization-free allylation and benzylation of alpha-hydroxyesters and the enantiopure synthesis of a chiral diglycole

O-Allylations and O-benzylations of alpha -hydroxy esters (3a-3c) are perfo rmed without racemization. The reagents applied, O-allyl- and O-benzyltrich loroacetimidate (5a, 5b) are prepared and converted in a one-pot-procedure. After protection by benzylation (S)-(-)-ethyl lactate (3a) is converted by a sequence of carbonyl reduction, alcohol activation, ether formation, and deprotection to the optically active diglycole derivative 1a.