Stereoselective aza-Diels–Alder reactions with 2H-azirines as dienophiles furnishing highly functionalized tetrahydropyridines

Highly diastereoselective Lewis acid mediated aza-Diels–Alder reactions of chiral auxiliary derivatized 2H-azirines have been accomplished for the first time, yielding bi and tri-cyclic heterocyclic compounds, comprising aziridine and tetrahydropyridine substructures, in up to 97% de; with the absolute stereochemistry of the major product confirmed by X-ray crystallography.