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

摘要

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. (C) 2015 Elsevier Ltd. All rights reserved.