Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

被引:50
|
作者
Falconnet, Alban [1 ]
Magre, Marc [1 ]
Maity, Bholanath [2 ]
Cavallo, Luigi [2 ]
Rueping, Magnus [1 ,2 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia
关键词
asymmetric reduction; DFT calculation; hydroboration; ketones; magnesium; ENANTIOSELECTIVE REDUCTION; HYDRIDE COMPLEXES; REACTIVITY; KETONES; DESYMMETRIZATION; BORANE; MECHANISM; ALDEHYDES; DIBORANE; REAGENTS;
D O I
10.1002/anie.201908012
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric catalysis with readily available, cheap, and non-toxic alkaline earth metal catalysts represents a sustainable alternative to conventional synthesis methodologies. In this context, we describe the development of a first Mg-II-catalyzed enantioselective hydroboration providing the products with excellent yields and enantioselectivities. NMR spectroscopy studies and DFT calculations provide insights into the reaction mechanism and the origin of the enantioselectivity which can be explained by a metal-ligand cooperative catalysis pathway involving a non-innocent ligand.
引用
收藏
页码:17567 / 17571
页数:5
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