title: Enantioselective synthesis of polycyclic nitrogen heterocycles by Rh-catalyzed alkene hydroacylation: constructing six-membered rings in the absence of chelation assistance.
abstract: Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.
authors.affiliation: Department of Chemistry, Iowa State University , 1605 Gilman Hall, Ames, Iowa 50014, United States.
authors.forename: Xiang-Wei
authors.initials: XW
authors.lastname: Du
authors.forename: Avipsa
authors.initials: A
authors.lastname: Ghosh
authors.forename: Levi M
authors.initials: LM
authors.lastname: Stanley
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D002614:Chelating Agents; D006571:Heterocyclic Compounds; D007659:Ketones; D012238:Rhodium; D009584:Nitrogen