The chiral structure of antibiotic vancomycin (Van) was exploited as an innovative coordination sphere for the preparation of an IrCp* based hybrid catalysts. We found that Van is able to coordinate iridium (Ir(III)) and the complexation was demonstrated by several analytical techniques such as MALDI-TOF, UV, Circular dichroism (CD), Raman IR, and NMR. The hybrid system so obtained was employed in the Asymmetric Transfer Hydrogenation (ATH) of cyclic imines allowing to obtain a valuable 61% e.e. (R) in the asymmetric reduction of quinaldine 2. The catalytic system exhibited a saturation kinetics with a calculated eciency of Kcat/KM = 0.688 h1mM1
Vancomycin-Iridium (III) Interaction: An Unexplored Route for Enantioselective Imine Reduction / G. Facchetti, S. Pellegrino, R. Bucci, D. Nava, R. Gandolfi, M. Christodoulou, I. Rimoldi. - In: MOLECULES. - ISSN 1420-3049. - 24:15(2019 Aug). [10.3390/molecules24152771]
Vancomycin-Iridium (III) Interaction: An Unexplored Route for Enantioselective Imine Reduction
G. FacchettiPrimo
;S. PellegrinoSecondo
;R. Bucci;D. Nava;R. Gandolfi;M. ChristodoulouPenultimo
;I.S. Rimoldi
Ultimo
2019
Abstract
The chiral structure of antibiotic vancomycin (Van) was exploited as an innovative coordination sphere for the preparation of an IrCp* based hybrid catalysts. We found that Van is able to coordinate iridium (Ir(III)) and the complexation was demonstrated by several analytical techniques such as MALDI-TOF, UV, Circular dichroism (CD), Raman IR, and NMR. The hybrid system so obtained was employed in the Asymmetric Transfer Hydrogenation (ATH) of cyclic imines allowing to obtain a valuable 61% e.e. (R) in the asymmetric reduction of quinaldine 2. The catalytic system exhibited a saturation kinetics with a calculated eciency of Kcat/KM = 0.688 h1mM1File | Dimensione | Formato | |
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