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
Artikel i vetenskaplig tidskrift, 2008

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 side-chain 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 α-methylation of the complexes was assessed using a model tyrosine-derived compound.

protective groups

alpha-methyl amino acids

circular dichroism

chiral synthon

Nickel

Schiff base

Författare

Milan Nadvornik

University of Pardubice

Vratislav Langer

Chalmers, Kemi- och bioteknik, Oorganisk miljökemi

Robert Jirasko

University of Pardubice

Michal Holcapek

University of Pardubice

Tomas Weidlich

University of Pardubice

Antonin Lycka

Vuzkumnu ustav organickuch syntez a.s

Alexander Popkov

Rijksuniversiteit Groningen

Polyhedron

0277-5387 (ISSN)

Vol. 27 3477-3483

Ämneskategorier

Oorganisk kemi

Läkemedelskemi

Miljövetenskap

Organisk kemi

DOI

10.1016/j.poly.2008.08.009