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Pregled bibliografske jedinice broj: 706979

"Backdoor induction" of chirality: asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted beta-turn mimetics


Kokan, Zoran; Glasovac, Zoran; Majerić Elenkov, Maja; Gredičak, Matija; Jerić, Ivanka; Kirin, Srećko I.
"Backdoor induction" of chirality: asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted beta-turn mimetics // Organometallics, 33 (2014), 15; 4005-4015 doi:10.1021/om5005385 (međunarodna recenzija, članak, znanstveni)


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Naslov
"Backdoor induction" of chirality: asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted beta-turn mimetics

Autori
Kokan, Zoran ; Glasovac, Zoran ; Majerić Elenkov, Maja ; Gredičak, Matija ; Jerić, Ivanka ; Kirin, Srećko I.

Izvornik
Organometallics (0276-7333) 33 (2014), 15; 4005-4015

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
amino acids; artificial metalloenzymes; asymmetric catalysis; DFT calculations; metallated bioconjugates; supramolecular chemistry

Sažetak
Bioconjugate bidentate ligands 2−10 were 8 obtained by tethering triphenylphosphanecarboxylic acid to amino acid substituted spacers with different flexibility, ranging from a rigid enediyne-based β-turn inducer to flexible linear aliphatic chains with up to eight carbon atoms. The 21 synthesized ligands revealed up to 81% ee selectivity in rhodium-catalyzed asymmetric hydrogenation of α, β-unsaturated amino acids. The key feature of the catalysts is the prochiral coordination sphere of the catalytic metal while the chirality is transmitted by “backdoor induction” from distant hydrogen-bonded amino acids. DFT calculations were applied to study the structure and relative stability of the precatalytic organometallic Rh(I) complexes, with particular emphasis on hydrogen-bonded secondary structures.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
3173 - Metalirani biokonjugati za primjene u istraživanju materijala i u biomedicini (MBABMS) (Srećko Kirin, HRZZ)
2309 - Višenuklearni metalni sustavi: sinteza i svojstva (Berislav Perić, )
906 - Kiralni građevni blokovi za biološki aktivne molekule. Sinteza i reaktivnost (Zdenko Hameršak, )
2184 - Kemijske preobrazbe prirodnih spojeva (Lidija Varga-Defterdarović, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Citiraj ovu publikaciju

Kokan, Zoran; Glasovac, Zoran; Majerić Elenkov, Maja; Gredičak, Matija; Jerić, Ivanka; Kirin, Srećko I.
"Backdoor induction" of chirality: asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted beta-turn mimetics // Organometallics, 33 (2014), 15; 4005-4015 doi:10.1021/om5005385 (međunarodna recenzija, članak, znanstveni)
Kokan, Z., Glasovac, Z., Majerić Elenkov, M., Gredičak, M., Jerić, I. & Kirin, S. (2014) "Backdoor induction" of chirality: asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted beta-turn mimetics. Organometallics, 33 (15), 4005-4015 doi:10.1021/om5005385.
@article{article, year = {2014}, pages = {4005-4015}, DOI = {10.1021/om5005385}, keywords = {amino acids, artificial metalloenzymes, asymmetric catalysis, DFT calculations, metallated bioconjugates, supramolecular chemistry}, journal = {Organometallics}, doi = {10.1021/om5005385}, volume = {33}, number = {15}, issn = {0276-7333}, title = {"Backdoor induction" of chirality: asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted beta-turn mimetics}, keyword = {amino acids, artificial metalloenzymes, asymmetric catalysis, DFT calculations, metallated bioconjugates, supramolecular chemistry} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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