title: Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation.
abstract: An enantioselective synthesis of almorexant, a potent antagonist of human orexin receptors, is presented. The chiral tetrahydroisoquinoline core structure was prepared via iridium-catalysed asymmetric intramolecular allylic amidation. Further key catalytic steps of the synthesis include an oxidative Heck reaction at room temperature and a hydrazine-mediated organocatalysed reduction.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands. m.fananas.mastral@rug.nl
authors.forename: Martín
authors.initials: M
authors.lastname: Fañanás-Mastral
authors.forename: Johannes F
authors.initials: JF
authors.lastname: Teichert
authors.forename: José Antonio
authors.initials: JA
authors.lastname: Fernández-Salas
authors.forename: Dorus
authors.initials: D
authors.lastname: Heijnen
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis*; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D006801:Humans; D007495:Iridium / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis*; D000068796:Orexin Receptor Antagonists; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D000577:Amides; D007546:Isoquinolines; D000068796:Orexin Receptor Antagonists; D007495:Iridium; C519150:almorexant