title: On the stereoselective bicyclization of aminodienes catalyzed by chelating diamide complexes of the group 3 metals. A direct comparison of Sc(III) and Y(III) bis(amide)s with an application to the synthesis of alkaloid 195F.
abstract: Highly diastereoselective bicyclizations of aminodienes catalyzed by chelating diamide complexes of Sc(III) and Y(III) that lead to pyrrolizidines and indolizidines are described. This bis(annulation) procedure has been utilized in a concise synthesis of the pyrrolizidine alkaloid 195F.
authors: Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA.
authors: Tao
authors: T
authors: Jiang
authors: Tom
authors: T
authors: Livinghouse
authors: Helena M
authors: HM
authors: Lovick
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry; D056831:Coordination Complexes / Q000737:chemistry*; D003500:Cyclization; D054836:Indolizidines / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D012538:Scandium / Q000737:chemistry; D013237:Stereoisomerism; D015019:Yttrium / Q000737:chemistry
chemical_list: D000577:Amides; D002614:Chelating Agents; D056831:Coordination Complexes; D054836:Indolizidines; D008670:Metals; D011763:Pyrrolizidine Alkaloids; D015019:Yttrium; D012538:Scandium