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Pregled bibliografske jedinice broj: 972347

"Backdoor induction" of chirality: Trans‐1, 2‐cyclohexanediamine as key building block for asymmetric hydrogenation catalysts


Opačak, Saša; Kokan, Zoran; Glasovac, Zoran; Perić, Berislav; Kirin, Srećko I.
"Backdoor induction" of chirality: Trans‐1, 2‐cyclohexanediamine as key building block for asymmetric hydrogenation catalysts // European journal of organic chemistry, 2019 (2019), 11; 2115-2128 doi:10.1002/ejoc.201801647 (međunarodna recenzija, članak, znanstveni)


Naslov
"Backdoor induction" of chirality: Trans‐1, 2‐cyclohexanediamine as key building block for asymmetric hydrogenation catalysts

Autori
Opačak, Saša ; Kokan, Zoran ; Glasovac, Zoran ; Perić, Berislav ; Kirin, Srećko I.

Izvornik
European journal of organic chemistry (1434-193X) 2019 (2019), 11; 2115-2128

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

Ključne riječi
Enantioselective catalysis ; backdoor induction ; hydrogenation ; supramolecular ; chirality transfer

Sažetak
This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine-tuning the steric and/or electronic properties. Cis square-planar metal complexes of Rh(I) and Pt(II) with ML2 stoichiometry have been prepared and characterized by spectroscopic methods (NMR, IR, UV-Vis, CD) and DFT calculations. Key feature of the metal complexes is a prochiral metal coordination sphere and "backdoor induction" of chirality from a distant chiral source via an outer-coordination sphere, welldefined by aromatic stacking and hydrogen-bonding. The rhodium complexes were used as catalysts in asymmetric hydrogenation of α, β-dehydroamino acids with excellent yield and selectivity (up to 97% ee), strongly supporting the "backdoor induction" hypothesis.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-1461 - Minimalni umjetni enzimi: Proširenje primjene posredne indukcije na nove supstrate i nove asimetrične reakcije (Srećko Kirin, )

Ustanove
Institut "Ruđer Bošković", Zagreb

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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