Vancomycin-Iridium (III) Interaction: An Unexplored Route for Enantioselective Imine Reduction

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Giorgio FacchettiIsabella Rimoldi

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 efficiency of Kcat/KM = 0.688 h-1mM-1.

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Citations

Oct 24, 2020·Journal of Peptide Science : an Official Publication of the European Peptide Society·Isabella RimoldiSara Pellegrino

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Methods Mentioned

BETA
Circular
NMR
X-ray

Software Mentioned

Jasco

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