Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines

Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines

A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good y...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2008-12, Vol.10 (23), p.5497-5499
Hauptverfasser: Barbe, Guillaume, St-Onge, Miguel, Charette, André B
Format: Artikel
Sprache:eng
Schlagworte:
Iodides - chemistry
Piperidines - chemical synthesis
Piperidines - chemistry
Silver - chemistry
Stereoisomerism
Substrate Specificity
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good yields and further derivatized to polysubstituted indolizidine.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8024605