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Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis
Rodolfo Lavilla1, M Carmen Bernabeu, Inés Carranco
1Parc Científic de Barcelona, University of Barcelona, Josep Samitier 1-5, 08028-Barcelona, Spain. rlavilla@pcb.ub.es
Organic Letters
|February 28, 2003
Abstract:
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.