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

Molecules

Donatella Nava¹  Giorgio Facchetti¹  Isabella Rimoldi¹  Raffaella Gandolfi¹  Sara Pellegrino¹  Raffaella Bucci¹  MichaelS. Christodoulou¹ 

[1] Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy;

关键词: glycopeptides;    hybrid catalyst;    asymmetric hydrogen transfer;   

DOI  :  10.3390/molecules24152771

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown