Tartaric acid and its O-acyl derivatives. Part 14: Nucleophilic ring-opening reaction of nonsymmetrically substituted tartaric acid anhydride as a tool for the synthesis of totally differentiated tartaric acid derivatives

Selective Formation of Monoacylated Diols through a Mild Passerini Reaction

“…Acyl migrations have been encountered in carbohydrate chemistry, where they may significantly disturb a designed synthetic route . Such an intramolecular acyl migration to explain the formation of isomers cannot be excluded here . To determine the rate of interconversion of the two regioisomers and the position of equilibrium, isomeric ratio at various reaction times was monitored by 1 H NMR spectroscopy (Table S1 in the Supporting Information).…”