"Backdoor induction" of chirality: asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted beta-turn mimetics (CROSBI ID 207507)
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Podaci o odgovornosti
Kokan, Zoran ; Glasovac, Zoran ; Majerić Elenkov, Maja ; Gredičak, Matija ; Jerić, Ivanka ; Kirin, Srećko I.
engleski
"Backdoor induction" of chirality: asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted beta-turn mimetics
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.
amino acids; artificial metalloenzymes; asymmetric catalysis; DFT calculations; metallated bioconjugates; supramolecular chemistry
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