Reactivity and stereoselectivity of the Diels–Alder reaction using cyclic dienophiles and siloxyaminobutadienes

Abstract

Several bicyclic compounds were synthesized by the Diels–Alder reaction using aminodiene and a cyclic dienophile. The stereochemistries of the obtained adducts were determined by X-ray crystallography or NMR analysis. The stereoselectivity of this Diels–Alder reaction was based on the interaction of molecular orbitals between the diene and dienophile. The reactivities of these Diels–Alder reactions were estimated, and the generality of this reaction is discussed.