title: Efficient Synthesis of β-Aryl-γ-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen.
abstract: An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)- and (S)-Baclofen hydrochloride.
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, Mexico. natzelane_k@hotmail.com.
authors.forename: Iris J
authors.initials: IJ
authors.lastname: Montoya-Balbás
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, Mexico. b.valentinguevara@gmail.com.
authors.forename: Berenice
authors.initials: B
authors.lastname: Valentín-Guevara
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, Mexico. fa_pple@hotmail.com.
authors.forename: Estefanía
authors.initials: E
authors.lastname: López-Mendoza
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, Mexico. linzaga@uaem.mx.
authors.forename: Irma
authors.initials: I
authors.lastname: Linzaga-Elizalde
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, Mexico. palacios@uaem.mx.
authors.forename: Mario
authors.initials: M
authors.lastname: Ordoñez
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, Mexico. rperl@uaem.mx.
authors.forename: Perla
authors.initials: P
authors.lastname: Román-Bravo
mesh_terms: D001418:Baclofen / Q000138:chemical synthesis*; D002384:Catalysis; D007769:Lactams / Q000138:chemical synthesis*; D009288:Naproxen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D009288:Naproxen; D001418:Baclofen
keywords: (S)-naproxen; Michael addition; baclofen; phenibut; resolution; β-aryl-γ-lactams