Asymmetric Synthesis of Methylphenidate and Quinolizidinones by Addition of Aldehydes to Piperidine-Based Conjugated N-Acyl­iminium Ions

Dedicated to Prof. Paolo Crotti on the occasion of his 70th birthday

Abstract

The synergistic effect of Lewis acids and MacMillan organocatalyst allows the α-regioselective and enantioselective α-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.

Key words

conjugated acyliminium - organocatalysis - asymmetric synthesis - α-amidoalkylation - aldehydes - tetrahydropyridines - quinolizidine alkaloids

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