title: Modular, flexible, and stereoselective synthesis of pyrroloquinolines: rapid assembly of complex heterocyclic scaffolds.
abstract: A novel 1,2-dinucleophile engages two imines in a sequential vinylogous Mannich-Mannich-Pictet-Spengler process to generate complex hexahydropyrrolo[3,2-c]quinolines in a one-pot operation. This methodology provides a rapid, highly modular, and flexible access toward a wide range of products and forms four new σ-bonds and chiral centers each. The diastereoselectivity may be inverted by fine-tuning of reaction conditions and the electronic nature of the imines.
authors.affiliation: Department of Organic Chemistry, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Boomhoff
authors.affiliation: Department of Organic Chemistry, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Yadav
authors.affiliation: Department of Organic Chemistry, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Appun
authors.affiliation: Department of Organic Chemistry, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Schneider
mesh_terms: D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007097:Imines; D011758:Pyrroles; D011804:Quinolines; C410406:pyrroloquinoline