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
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Date
2014-02-19Author
Moriwaki, Hiroki
Resch, Daniel
Li, Hengguang
Ojima, Iwao
Takeda, Ryosuke
Aceña Bonilla, José Luis
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Beilstein Journal of Organic Chemistry 10 : 442-448 (2014)
Abstract
A family of chiral ligands derived from alpha-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.