Silver ion-induced Grob fragmentation of gamma-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 yields and further derivatized to polysubstituted indolizidine.
Barbe
Guillaume
G
Departement de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
St-Onge
Miguel
M
Charette
André B
AB
D007454:Iodides / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007454:Iodides; D010880:Piperidines; D012834:Silver; C032727:piperidine