Sustainable synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived carboxylic acids?

Chemical Communications Pub Date: 2020-06-01 DOI: 10.1039/D0CC02163F

Abstract

Herein, we report a sustainable route for the synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived muconic acid and fumaric acid. The key Diels–Alder reaction constructed a cyclohexene framework substituted by four ester groups. The isolated yield of tetramethyl 5-cyclohexene-1,2,3,4-tetracarboxylate was up to 95.5% without any catalyst used. And the hydrogenation reaction of the cycloadduct was catalyzed by commercial RANEY? Ni at room temperature and nearly 100% yield of the cyclohexyl target products was obtained.

Graphical abstract: Sustainable synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived carboxylic acids
Recommended Literature