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Substituted 1,2,3,4-tetrahydroquinolines and related N-heterocycles are formed highly regio- and diastereoselectively with yields ranging from 57 to 100% by intermolecular polar (4π + + 2π) cycloadditions of cationic 2-azabutadienes and various dienophiles. The cationic 2- azabutadienes can be generated in situ by Lewis acid mediated heterolytic cleavage of N,S- acetals. Best results have been obtained using a new mixed Lewis acid consisting of a mixture of TiCl4 and PPh3.

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Generation of cationic 2-azabutadienes from N,S-acetals and their use for the regio- and diastereoselective synthesis of 1,2,3,4-tetrahydroquinolines by intermolecular [4p+ + 2p] cycloadditions