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

The ring-opening reaction of nonsymmetrically substituted tartaric acid anhydride was used to synthesize monoamides and monoesters of O-benzoyltartaric acid, type I (a) and II (b) building blocks with all four functional groups differentiated. The correct structure of the regioisomers, which had earlier been misassigned, was established. The type I-type II regioisomer rearrangement, which proceeded via acyl migration, was examined. Moreover, it was shown that acyl migration induced by selective crystallization may yield one of the regioisomers quantitatively.

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