Improved Dienophilicity of Nitrocycloalkenes: Prospects for the Development of a trans-Diels-Alder Paradigm

The development of an efficient and stereoselective trans-Diels-Alder paradigm is described. A central element of this transformation is the introduction of a temporary dienophilic functionality (A), which serves both to activate the substrate for Diets-Alder cycloaddtion and, through its subsequent removal, to facilitate conversion of the cis-fused cycloadducts to the trans-fused series.