Enantioselective Cycloaddition of in Situ Formed aza-Dienes and Vinyl Diazo Compounds for the Synthesis of Optically Enriched and Diazo Containing Tetrahydropyridazine.

A copper catalyzed enantioselective formal aza-Diels-Alder reaction of in situ formed 1,2-diaza-1,3-dienes from α-halohydrazones and vinyl diazo compounds was described. The protocol provides a variety of optically enriched diazo-containing tetrahydropyridazines in moderate yields and with up to excellent enantioselectivities. The present methodologies utilize chiral oxazolines as the chiral ligands for asymmetric catalysis and feature mild reaction conditions, readily available substrates, and broad substrate scope.