Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

Alban Falconnet; Marc Magre; Bholanath Maity; Luigi Cavallo; Magnus Rueping

doi:10.1002/ange.201908012

Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

Alban Falconnet, Marc Magre, Bholanath Maity, Luigi Cavallo, Magnus Rueping

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

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.

Original language	English (US)
Pages (from-to)	17731-17735
Number of pages	5
Journal	Angewandte Chemie
Volume	131
Issue number	49
DOIs	https://doi.org/10.1002/ange.201908012 https://doi.org/10.1002/anie.201908012
State	Published - Oct 23 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: B.M. and L.C. acknowledge King Abdullah University of Science and Technology (KAUST) for computational resources of the supercomputer Shaheen II

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title = "Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis",

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.",

author = "Alban Falconnet and Marc Magre and Bholanath Maity and Luigi Cavallo and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: B.M. and L.C. acknowledge King Abdullah University of Science and Technology (KAUST) for computational resources of the supercomputer Shaheen II",

year = "2019",

month = oct,

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doi = "10.1002/ange.201908012",

language = "English (US)",

volume = "131",

pages = "17731--17735",

journal = "Angewandte Chemie",

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TY - JOUR

T1 - Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

AU - Falconnet, Alban

AU - Magre, Marc

AU - Maity, Bholanath

AU - Cavallo, Luigi

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: B.M. and L.C. acknowledge King Abdullah University of Science and Technology (KAUST) for computational resources of the supercomputer Shaheen II

PY - 2019/10/23

Y1 - 2019/10/23

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/659512

UR - https://onlinelibrary.wiley.com/doi/abs/10.1002/ange.201908012

U2 - 10.1002/ange.201908012

DO - 10.1002/ange.201908012

M3 - Article

C2 - 31642572

SN - 0044-8249

VL - 131

SP - 17731

EP - 17735

JO - Angewandte Chemie

JF - Angewandte Chemie

IS - 49

ER -

Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

Abstract

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