Nucleophilic substitution without neighbouring acyloxy-group participation. Reaction of acylglycerols with the reagent system triphenylphosphine–diethyl azodicarboxylate–carboxylic acid

Abstract

Nucleophilic substitution of HO by RCO₂ at C-2 in acylglycerol derivatives proceeds without acyloxy migration from C-1/C-3 in a ready reaction with the triphenylphosphine-diethyl azodicarboxylate-carboxylic acid reagent system; the reaction is useful for the transformations of partially acylated chiral glycerides into carboxylic esters of the enantiomeric series.