title: Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines.
abstract: A convenient trans-selective one-pot synthesis of tetrafunctionalized 2-imidazolines is described. Our approach to these valuable heterocyclic scaffolds involves a formal 1,3-dipolar cycloaddition between nitrile ylides or nitrilium triflates and imines. A detailed experimental study in combination with a high-level computational exploration of reaction routes reveals a plausible reaction pathway that accounts for the observed diastereoselectivity.
authors.affiliation: Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), VU University Amsterdam , De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.
authors.forename: Guido V
authors.initials: GV
authors.lastname: Janssen
authors.forename: Paul
authors.initials: P
authors.lastname: Slobbe
authors.forename: Maurice
authors.initials: M
authors.lastname: Mooijman
authors.forename: Art
authors.initials: A
authors.lastname: Kruithof
authors.forename: Andreas W
authors.initials: AW
authors.lastname: Ehlers
authors.forename: Célia Fonseca
authors.initials: CF
authors.lastname: Guerra
authors.forename: F Matthias
authors.initials: FM
authors.lastname: Bickelhaupt
authors.forename: J Chris
authors.initials: JC
authors.lastname: Slootweg
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
authors.forename: Koop
authors.initials: K
authors.lastname: Lammertsma
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D048288:Imidazolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D007093:Imidazoles; D048288:Imidazolines; D009570:Nitriles; C017424:2-imidazoline