title: Chiral phosphoric acid-catalyzed enantioselective three-component Povarov reaction using cyclic enethioureas as dienophiles: stereocontrolled access to enantioenriched hexahydropyrroloquinolines.
abstract: Three become one: Phosphoric acid-catalyzed enantioselective three-component Povarov reactions of aldehydes, anilines, and endocyclic enethioureas have been developed (see scheme). This process afforded hexahydropyrroloquinolines in high yields with excellent diastereo- and enantioselectivities. The presence of the thiourea functionality is crucial for the enantioselectivity of the reaction.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Dagousset
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Géraldine
authors.initials: G
authors.lastname: Masson
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D029402:Bignoniaceae / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D018749:RNA, Plant / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000814:Aniline Compounds; D010756:Phosphoric Acids; D011758:Pyrroles; D011804:Quinolines; D018749:RNA, Plant; C410406:pyrroloquinoline; D013890:Thiourea