Diels-Alder cycloadditions of rigid dienophiles: A probe for allylic axial substituent control of the pi-facial selectivity in the Diels-Alder reaction

Summary A study of the pi-facial selectivity of the Diels-Alder reaction of N -benzoyl 5-methoxycarbony 1–2-aza-oxabicyclo[2.2.2]oct-4-ene, a rigid electron deficient dienophile bearing two allylic axial heteroatom substituents, with 1-methoxy-3-trimethylsilyloxybutadiene, a representative electron rich diene, is detailed.