title: The use of phosphite-type ligands in the Ir-catalyzed asymmetric hydrogenation of heterocyclic compounds.
abstract: A series of chiral phosphite-type ligands was tested in asymmetric Ir-catalyzed hydrogenation of quinolines and 2,4,5,6-tetrahydro-1H-pyrazino(3,2,1-j,k)carbazole. Hydrogenation of quinaldine hydrochloride provided superior enantioselectivity up to 65% ee compared to quinaldine free base. The ligands were tested for the first time in the asymmetric Ir-Ircatalyzed hydrogenation of 2,4,5,6-tetrahydro-1H-pyrazino(3,2,1-j,k)carbazole yielding the antidepressant drug, pirlindole.
authors.affiliation: Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia.
authors.forename: Sergey E
authors.initials: SE
authors.lastname: Lyubimov
authors.forename: Dmitry V
authors.initials: DV
authors.lastname: Ozolin
authors.forename: Pavel Yu
authors.initials: PY
authors.lastname: Ivanov
authors.forename: Artem
authors.initials: A
authors.lastname: Melman
authors.forename: Valeriya S
authors.initials: VS
authors.lastname: Velezheva
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Davankov
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D017905:Phosphites / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D008024:Ligands; D017905:Phosphites; D007495:Iridium
keywords: asymmetric hydrogenation; phosphites; pirlindole; quinaldine hydrochloride