Asymmetric Synthesis Of Methylphenidate And Quinolizidinones By Addition Of Aldehydes To Piperidine-Based Conjugated N-Acyliminium Ions

The synergistic effect of Lewis acids and MacMillan organocatalyst allows the -regioselective and enantioselective -amidoalkylation of piperidine derivatives with enolizable aldehydes. The potentiality of the synthetic method is illustrated by a short asymmetric synthesis of the eutomer of the blockbuster drug Ritalin and by a concise formal synthesis of 1-alkyl-4-substituted quinolizidine alkaloids.