title: Diastereo- and enantioselective hydrogenation of a challenging enamide derived from 4-phenyl-2-tetralone: an appealing shortcut towards enantiopure cis-2-aminotetraline derivatives.
abstract: A clean, efficient, and diasteroselective (dr >95%) catalytic hydrogenation of the enamide N-(4-phenyl-3,4-dihydronaphthalen-2-yl)propionamide (2 a) using palladium on carbon is performed. This procedure provides the melatonin receptor ligand (+/-)-cis-4-phenyl-2-propionamidotetralin (cis-4-P-PDOT, 1 a) and its 8-methoxy analog. Furthermore, Rh and Ru catalyzed homogeneous asymmetric hydrogenation of the challenging racemic endocyclic enamide 2 a with several chiral phosphine ligands is studied. The best results, in terms of enantioselectivity, for both diastereomers are obtained when chiral Rh-Josiphos is used as the catalyst.
authors.affiliation: Institute of Medicinal Chemistry, University of Urbino Carlo Bo, Piazza Rinascimento 6, 61029 Urbino (PU), Italy. simone.lucarini@uniurb.it
authors.forename: Simone
authors.initials: S
authors.lastname: Lucarini
authors.forename: Matteo
authors.initials: M
authors.lastname: Alessi
authors.forename: Annalida
authors.initials: A
authors.lastname: Bedini
authors.forename: Giorgia
authors.initials: G
authors.lastname: Giorgini
authors.forename: Giovanni
authors.initials: G
authors.lastname: Piersanti
authors.forename: Gilberto
authors.initials: G
authors.lastname: Spadoni
mesh_terms: D000577:Amides; D006865:Hydrogenation; D008024:Ligands; D044094:Receptors, Melatonin; D012238:Rhodium; D012428:Ruthenium; D013237:Stereoisomerism; D044024:Tetralones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000577:Amides; D008024:Ligands; D044094:Receptors, Melatonin; D044024:Tetralones; D012428:Ruthenium; D012238:Rhodium