title: Synergistic rhodium(II) carboxylate and brønsted acid catalyzed multicomponent reactions of enalcarbenoids: direct synthesis of α-pyrrolylbenzylamines.
abstract: The design of a synergistic rhodium(II) carboxylate and BINOL phosphoric acid catalyzed efficient multicomponent reaction of enaldiazo compounds, arylamines, and aryl aldehydes leading to the first transition-metal-catalyzed direct synthesis of valuable α-pyrrolylbenzylamines is disclosed. The reaction is proposed to involve a transient ammonium ylide of a new class of electrophilic rhodium enalcarbenoid, its regioselective Mannich reaction, and a cyclocondensation cascade. The methodology was used in a highly diastereoselective synthesis of a binaphthyl based chiral pyrrole.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education & Research , Bhopal, Madhya Pradesh 462066, India.
authors.forename: Sudam Ganpat
authors.initials: SG
authors.lastname: Dawande
authors.forename: Vinaykumar
authors.initials: V
authors.lastname: Kanchupalli
authors.forename: Bapurao Sudam
authors.initials: BS
authors.lastname: Lad
authors.forename: Jyoti
authors.initials: J
authors.lastname: Rai
authors.forename: Sreenivas
authors.initials: S
authors.lastname: Katukojvala
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001596:Benzylamines / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001596:Benzylamines; D002264:Carboxylic Acids; D010756:Phosphoric Acids; D011758:Pyrroles; D012238:Rhodium; C030242:phosphoric acid