Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis
M. Sc. Alban Falconnet
Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
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Dr. Marc Magre
Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
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Dr. Bholanath Maity
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
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Prof. Dr. Luigi Cavallo
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
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Prof. Dr. Magnus Rueping
Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
Search for more papers by this authorM. Sc. Alban Falconnet
Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorCorresponding Author
Dr. Marc Magre
Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
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Dr. Bholanath Maity
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
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Prof. Dr. Luigi Cavallo
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
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Prof. Dr. Magnus Rueping
Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
Search for more papers by this authorGraphical Abstract
Mg-ligand cooperative activation of HBpin: The enantioselective magnesium-catalyzed hydroboration of ketones using a (R)-(+)-BINOL derivative as a chiral ligand affords excellent yields and enantioselectivities. Experimental investigations together with DFT calculations provide insight into the reaction mechanism and the origin of enantioselectivity.
Abstract
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 MgII-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.
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