Enantioselective (Formal) Aza-Diels−Alder Reactions with Non-Danishefsky-Type Dienes

Enantioselective (formal) aza-Diels−Alder reactions between acylhydrazones and non-Danishefsky-type dienes have been developed. The reactions are promoted by a simple and economical chiral silicon Lewis acid and are typically conducted at ambient temperature. Both glyoxylate- and aliphatic aldehyde-derived hydrazones may be employed, as may variously substituted dienes, leading to the synthesis of a diverse array of tetrahydropyridines with good to excellent levels of enantioselectivity.