title: Diastereoselective access to nonracemic 2-cis-substituted and 2,6-cis-disubstituted piperidines.
abstract: Access to nonracemic amino ketones via a hydrozirconation/transmetalation/acylation sequence applied to Boc-protected 1-aminobut-3-enes is presented. This method was applied to the stereoselective synthesis of cyclic imines (or iminiums) which were diastereoselectively converted into 2-cis-substituted and 2,6-cis-disubstituted piperidines. The potential of this approach in the field of alkaloid synthesis was illustrated by the synthesis of (-)-coniine and (-)-indolizidine 209D. Furthermore, access to indolizidines bearing a quaternary center could also be envisioned through this strategy.
authors: Institut de Chimie Moléculaire de Reims, CNRS (UMR 6229) and Université de Reims, 51687 Reims Cedex 2, France.
authors: Nicolas
authors: N
authors: Coia
authors: Naïma
authors: N
authors: Mokhtari
authors: Jean-Luc
authors: JL
authors: Vasse
authors: Jan
authors: J
authors: Szymoniak
mesh_terms: D000215:Acylation; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D054836:Indolizidines; D007212:Indolizines; D010880:Piperidines; C449379:indolizidine 209D; C007112:coniine