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Syntheses, X-ray, MSn, NMR and CD structure determination of nickel(II) complexes of Schiff bases of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and aromatic α-amino acids.
Authors: Nádvorník Milan | Langer Vratislav | Jirásko Robert | Holčapek Michal | Weidlich Tomáš | Lyčka Antonín | Popkov Alexander
Year: 2008
Type of publication: článek v odborném periodiku
Name of source: Polyhedron
Publisher name: Pergamon-Elsevier Science Ltd.
Place: Oxford
Page from-to: 3477-3483
Titles:
Language Name Abstract Keywords
cze Příprava a určení struktury metodami X-ray, MSn, NMR a CD komplexů niklu(II) se Schiffovými bázemi odvozenými od (S)-N-(2-benzoylfenyl)-1-benzylpyrrolidin-2-carboxamidu a aromatických α-aminokyselin. A preparative procedure for the synthesis of an important chiral synthon of side-chain protected tyrosine was developed and optimised for the minimisation of nickel salts waste. While preparing a similar sidechain protected tryptophan synthon, an unexpected low stability was found of the Boc-protective group of the tryptophan aromatic nitrogen during purification on silica gel. X-ray crystal structure determination, tandem mass spectrometry (MS/MS) and NMR were applied for the elucidation of the structures of the prepared complexes and by-products. Stereochemistry of products of a-methylation of the complexes was assessed using a model tyrosine-derived compound.
eng Syntheses, X-ray, MSn, NMR and CD structure determination of nickel(II) complexes of Schiff bases of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and aromatic α-amino acids. A preparative procedure for the synthesis of an important chiral synthon of side-chain protected tyrosine was developed and optimised for the minimisation of nickel salts waste. While preparing a similar sidechain protected tryptophan synthon, an unexpected low stability was found of the Boc-protective group of the tryptophan aromatic nitrogen during purification on silica gel. X-ray crystal structure determination, tandem mass spectrometry (MS/MS) and NMR were applied for the elucidation of the structures of the prepared complexes and by-products. Stereochemistry of products of a-methylation of the complexes was assessed using a model tyrosine-derived compound. Nickel Schiff base a-Methyl amino acids Chiral synthon Protective groups Circular dichroism

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