Naslov
Rh(I) catalyzed enantioselective hydrogenation using chiral monodentate pseudo-peptide ligands

Autori
Kokan, Zoran ; Kirin, Srećko I.

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
31st European Peptide Symposium / - , 2010, P-535

Skup
31st European Peptide Symposium

Mjesto i datum
Kopenhagen, Danska, 05.09.2010. - 09.09.2010

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
monodentatni ligandi; supramolekularna kemija; asimetrična kataliza
(monodentate ligands; supramolecular chemistry; asymmetric catalysis)

Sažetak
After the discovery of Wilkinson's homogenous hydrogenation catalyst [RhCl(PPh3)3], chiral phosphine ligands have been used in catalytic enantioselective hydrogenation, with particular emphasis on industrial pplications. Chelating bisphosphorous ligands generally show greater enantioselectivities if compared to monodentate ligands, but moderate to excelent enantioselectivities in catalytic hydrogenation can be achieved with monodentate phosphorous ligands as well. The advantages of monodentate ligands are easier synthesis and straightforward structural variations (ligand library), for finetuning the catalytic properties. Herein, enantionselective catalytic hydrogenation of the model substrate 2-acetamidoacrylate methyl ester is performed by the in situ formed Rh(I) complexes of monodentate triphenylphosphine derived ligands (L) with RhL2 stoichiometry. The ligands, monosubstituted with amino acid chains differing in lenght and peptide sequence (up to three amino acids), were obtained by coupling p-(diphenylphosphine)benzioc acid with the corresponding amino acid or peptide and fully characterized by spectroscopic methods. The catalysis results indicate positive correlation between enantioselectivity and the amino acid chain lenght.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA