Divergent pathways to isophthalates and naphthalate esters from methyl coumalate
Methyl coumalate readily reacts with enamines at ambient temperature to give lactones, which can be further transformed into isophthalates and tetrahydronaphthoates. Both cyclic and acyclic enamines show good reactivity. Dehydrogenation of tetrahydronaphthoate 4a was achieved on a hundred-gram scale.
This is a manuscript of an article published as Yu, Huangchao, and George A. Kraus. "Divergent pathways to isophthalates and naphthalate esters from methyl coumalate." Tetrahedron Letters 59, no. 45 (2018): 4008-4010. DOI: 10.1016/j.tetlet.2018.09.058. Posted with permission.