title: Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)amino]acetyl}amino)benzophenone; a case of configurationally stable stereogenic nitrogen.
abstract: A family of chiral ligands derived from α-phenylethylamine and 2-aminobenzophenone were prepared by alkylation of the nitrogen atom. Upon reaction with glycine and a Ni(II) salt, these ligands were transformed into diastereomeric complexes, as a result of the configurational stability of the stereogenic nitrogen atom. Different diastereomeric ratios were observed depending on the substituent R introduced in the starting ligand, and stereochemical assignments were based on X-ray analysis, along with NMR studies and optical rotation measurements.
authors.affiliation: Department of Chemistry, Institute of Chemical Biology & Drug Discovery, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, United States ; Hamari Chemicals Ltd. 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, Japan 533-0024.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Moriwaki
authors.affiliation: Department of Chemistry, Institute of Chemical Biology & Drug Discovery, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, United States.
authors.forename: Daniel
authors.initials: D
authors.lastname: Resch
authors.affiliation: Department of Chemistry, Institute of Chemical Biology & Drug Discovery, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, United States.
authors.forename: Hengguang
authors.initials: H
authors.lastname: Li
authors.affiliation: Department of Chemistry, Institute of Chemical Biology & Drug Discovery, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, United States.
authors.forename: Iwao
authors.initials: I
authors.lastname: Ojima
authors.affiliation: Hamari Chemicals Ltd. 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, Japan 533-0024.
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Takeda
authors.affiliation: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country, 20018 San Sebastián, Spain.
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.affiliation: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country, 20018 San Sebastián, Spain ; IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain.
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
keywords: Ni(II) complexes; Schiff bases; amino acids; asymmetric synthesis; stereogenic nitrogen