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万古霉素-铱(III)相互作用:手性亚胺还原的未知途径。

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

机构信息

Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy.

出版信息

Molecules. 2019 Jul 30;24(15):2771. doi: 10.3390/molecules24152771.

DOI:10.3390/molecules24152771
PMID:31366120
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6695689/
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% () in the asymmetric reduction of quinaldine . The catalytic system exhibited a saturation kinetics with a calculated efficiency of K/K = 0.688 hmM.

摘要

万古霉素(Van)的手性结构被用作一种创新的配位体,用于制备基于 IrCp*的杂化催化剂。我们发现 Van 能够与铱(Ir(III))配位,这种配位作用通过 MALDI-TOF、UV、圆二色性(CD)、拉曼 IR 和 NMR 等多种分析技术得到了证明。所得到的杂化体系被用于环状亚胺的不对称转移氢化(ATH)中,从而在喹啉的不对称还原中获得了有价值的 61%ee()。该催化体系表现出饱和动力学,计算效率为 K/K = 0.688 hmM。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad41/6695689/3ceb6f649750/molecules-24-02771-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad41/6695689/9e49fecec1f5/molecules-24-02771-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad41/6695689/a69415852735/molecules-24-02771-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad41/6695689/3ceb6f649750/molecules-24-02771-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad41/6695689/9e49fecec1f5/molecules-24-02771-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad41/6695689/a69415852735/molecules-24-02771-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad41/6695689/3ceb6f649750/molecules-24-02771-sch001.jpg

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