Samarium diiodide-induced intramolecular pinacol coupling of dinitrones: synthesis of cyclic cis-vicinal diamines.
Pinacol coupling of alkyl dinitrones mediated by SmI2 was achieved in the presence of a proton source allowing the synthesis of cyclic vicinal diamines with good cis-selectivity.
Ebran
Jean-Philippe
JP
Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000, Aarhus C, Denmark.
Hazell
Rita G
RG
Skrydstrup
Troels
T
D018360:Crystallography, X-Ray; D003500:Cyclization; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry; D011744:Pyrimidinones / Q000737:chemistry*; D012493:Samarium / Q000737:chemistry*
D003959:Diamines; D005960:Glucosides; D006571:Heterocyclic Compounds; D006835:Hydrazones; D007454:Iodides; D009589:Nitrogen Oxides; D010091:Oximes; D011744:Pyrimidinones; C015388:nitrones; D012493:Samarium; C009661:vicine; C409809:samarium diiodide