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

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 K_cat/K_M = 0.688 h^-1mM^-1.

SUBMITTER: Facchetti G

PROVIDER: S-EPMC6695689 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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

Facchetti Giorgio G Pellegrino Sara S Bucci Raffaella R Nava Donatella D Gandolfi Raffaella R Christodoulou Michael S MS Rimoldi Isabella I

Molecules (Basel, Switzerland) 20190730 15

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% <i>e ...[more]

PMID: 31366120

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