Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels–Alder Reaction of ortho-Quinone Methide Imines

Aza-Diels–Alder reactions are straightforward processes for the construction of N-heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow the formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid bound ortho-quinone methide imines to generate a range of interesting fused tetrahydroquinolines in a diastereo- and enantioselective­ manner.