The tetrahydroquinoline moiety is an important structural component of a number of natural products. The reaction of aryl azides with 2,3-dihydro-2H-furan and 3,4-dihydro-2H-pyran in the presence of chlorotrimethyl silane- sodium iodide (TMSCl-NaI) affords the corresponding 1,2,3,4-tetrahydroquinoline derivatives in an efficient manner and most of these compounds exhibited cis selectivity. The aza-Diels-Alder reaction may proceed through in situ generation of aryl amines followed by the reaction between 2-azadiene and another equivalent of cyclic enol resulting in the formation of 1,2,3,4-tetrahydroquinolines. (c) 2007 Elsevier B.V. All rights reserved.