Bismuth triflate catalyzed condensation of δ-hydroxy-α, β-unsaturated aldehydes with aryl amines

alpha,beta-Unsaturated aldehydes bearing a delta-hydroxyl group undergo a tandem Michael and intramolecular Friedel-Crafts type cyclization with arylamines in the presence of 5 mol% of Bi(OTF)(3) under mild conditions to afford a new class of chiral tetrahydroquiriolines in good yields with high stereoselectivity. Structural assignments and the stereochemistry of the products was achieved using various 1D and 2D-NMR experiments. (C) 2003 Elsevier Ltd. All rights reserved.