title: Redox cycloisomerization approach to 1,2-dihydropyridines.
abstract: The phosphine-catalyzed synthesis of 1,2-dihydropyridines via an alkyne isomerization/electrocyclization sequence is described. Propargylidenecarbamate substrates were prepared following a one-pot procedure between a terminal alkyne, a benzonitrile, and a chloroformate in the presence of trimethylaluminum. This methodology gives access to a diverse set of 2,6-disubstituted 1,2-dihydropyridines in high yield. The products can be easily converted into substituted piperidines or pyridines, and this methodology was applied to the synthesis of indolizidines.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5580, United States.
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5580, United States.
authors.forename: Berenger
authors.initials: B
authors.lastname: Biannic
mesh_terms: D000480:Alkynes / Q000737:chemistry; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D005561:Formates / Q000737:chemistry; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis; D011725:Pyridines / Q000138:chemical synthesis
chemical_list: D000480:Alkynes; D004095:Dihydropyridines; D005561:Formates; D054836:Indolizidines; D009570:Nitriles; D010880:Piperidines; D011725:Pyridines