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 block...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 48; no. 16; pp. 2645 - 2652
Main Authors Berti, Francesco, Favero, Lucilla, Pineschi, Mauro
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOSELECTIVE SYNTHESIS
conjugated acyliminium
ARYLATION
tetrahydropyridines
THREO-METHYLPHENIDATE
SALTS
organocatalysis
MANNICH REACTION
amidoalkylation
aldehydes
asymmetric synthesis
RING-CLOSING METATHESIS
HETEROCYCLES
quinolizidine alkaloids
DIALKYLZINC REAGENTS
LYCOPODIUM ALKALOIDS
DERIVATIVES
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1562486