Synthesis 2016; 48(16): 2645-2652
DOI: 10.1055/s-0035-1562486
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Francesco Berti
Dipartimento di Farmacia, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy   Email: pineschi@farm.unipi.it
,
Lucilla Favero
Dipartimento di Farmacia, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy   Email: pineschi@farm.unipi.it
,
Mauro Pineschi*
Dipartimento di Farmacia, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy   Email: pineschi@farm.unipi.it
› Author Affiliations
Further Information

Publication History

Received: 13 April 2016

Accepted after revision: 18 May 2016

Publication Date:
24 June 2016 (eFirst)

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.

Supporting Information

 
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