Synthesis of C1-Substituted 7-Oxanorbornadienes

Abstract

7-Oxanorbornadienes are valuable synthetic intermediates as they can serve as general templates to create highly substituted ring systems. However, to date, only very few C1-substituted 7-oxanorbornadienes have been synthesized and can be found in the literature. In this article, synthesis of some C1-substituted 7-oxanorbornadienes was achieved by the Diels–Alder reaction between 2-substituted furans and dimethylacetylene dicarboxylate. Moderate to good yields (13–85%) of the Diels–Alder reactions were observed. These C1-substituted 7-oxanorbornadienes will find applications as valuable synthetic intermediates and are useful in the studies of transition-metal-catalyzed reactions.