title: Nazarov reactions of vinyl cyclopropylamines: an approach to the imino-Nazarov problem.
abstract: Dichlorocyclopropanation of 2-amino-1,3-dienes affords 1-alkenyl-1-amino-2,2-dichlorocyclopropanes which undergo silver-assisted 2-π electrocyclic opening to furnish 3-aminopentadienyl cations. Nazarov-type cyclization of these intermediates leads to cyclopentenone iminium salts, which provide allylic amines upon reduction. This process, the imino version of the traditional Nazarov reaction, can also be combined with an interrupted Nazarov domino process to give polycyclic amines.
authors.affiliation: Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, Canada, T6G 2G2.
authors.forename: Sara A
authors.initials: SA
authors.lastname: Bonderoff
authors.forename: Tina N
authors.initials: TN
authors.lastname: Grant
authors.forename: F G
authors.initials: FG
authors.lastname: West
authors.forename: Martin
authors.initials: M
authors.lastname: Tremblay
mesh_terms: D002384:Catalysis; D002412:Cations / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D002412:Cations; D003517:Cyclopentanes; D003521:Cyclopropanes; D014753:Vinyl Compounds; D012834:Silver; C067351:cyclopropylamine