title: IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel-Crafts reactions.
abstract: The first o-iodoxybenzoic acid (IBX) mediated oxidation of unactivated amines to imines is described. A range of meso-pyrrolidines were shown to be suitable substrates. The chemical space was further explored with one-pot oxidative Ugi-type and aza-Friedel-Crafts reactions, which proved to be highly diastereoselective.
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands. r.v.a.orru@vu.nl.
authors.forename: C
authors.initials: C
authors.lastname: de Graaff
authors.forename: L
authors.initials: L
authors.lastname: Bensch
authors.forename: Matthijs J
authors.initials: MJ
authors.lastname: van Lint
authors.forename: E
authors.initials: E
authors.lastname: Ruijter
authors.forename: R V A
authors.initials: RV
authors.lastname: Orru
mesh_terms: D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000588:Amines; D001372:Aza Compounds; D007097:Imines; D007462:Iodobenzenes; C476101:o-iodoxybenzoic acid