Organic Letters · 2011 · 35 citations · 45 references
Natural SciencesChemistryMedicinal ChemistryBioorganic ChemistryOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisRetrosynthetic AnalysisKetonesPiperidine AlkaloidsPiperidine ChemistryPiperidine SynthesisStereocontrolled Library SynthesisStereoselective Synthesis
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.
45
Maxime G. P. Buffat · Tetrahedron · 2004 · 546 citations
Recent advances in the synthesis of piperidones and piperidines
Philip M. Weintraub, Jeffrey S. Sabol, John M. Kane et al. · Tetrahedron · 2003 · 458 citations
Synthetic applications of organochlorozirconocene complexes
Peter Wipf, Heike Jahn · Tetrahedron · 1996 · 294 citations