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1: Org Lett. 2003 Mar 6;5(5):717-20.Click here to read Links

Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions.

Parc Científic de Barcelona, University of Barcelona, Josep Samitier 1-5, 08028-Barcelona, Spain. rlavilla@pcb.ub.es

The three-component reaction of dihydropyridines, aldehydes, and p-methylaniline efficiently forms highly substituted tetrahydroquinolines in a stereoselective manner through a Lewis acid-catalyzed formal [4 + 2] cycloaddition. InCl(3) and Sc(OTf)(3) are the catalysts of choice for this process. The in situ generation of a reactive 1,4-dihydropyridine through the regioselective nucleophilic addition of cyanide to pyridinium salts allows a one-pot four-component transformation.

PMID: 12605498 [PubMed - indexed for MEDLINE]