Diels−Alder Reaction of Sugar-Derived Cyclic Dienophiles with Cyclopentadiene. Factors Affecting the Reactivity and Stereoselectivity

A sugar-derived cyclic dienophile showed a high exo and face selectivity in the Diels−Alder reaction with cyclopentadiene. Structural modifications on the dienophile structure were made, and the outcomes of the cycloaddition reactions were investigated. These results and the spectroscopic data recorded within a series of analogues were used to analyze the factors affecting the reactivity and exo selectivity.