Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.

Yury Lebedev; Iuliia Polishchuk; Bholanath Maity; Miguel Dinis Veloso Guerreiro; Luigi Cavallo; Magnus Rueping

doi:10.1021/jacs.9b10364

Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.

Yury Lebedev, Iuliia Polishchuk, Bholanath Maity, Miguel Dinis Veloso Guerreiro, Luigi Cavallo, Magnus Rueping

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

44 Scopus citations

Abstract

A series of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100-500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands in asymmetric catalysis. Isolation and comprehensive characterization of the reaction intermediates support a catalysis cycle proposed by DFT calculations.

Original language	English (US)
Pages (from-to)	19415-19423
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	141
Issue number	49
DOIs	https://doi.org/10.1021/jacs.9b10364
State	Published - Nov 8 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 support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.

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10.1021/jacs.9b10364

https://repository.kaust.edu.sa/bitstream/10754/660479/1/Manuscript-final.pdf

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title = "Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.",

abstract = "A series of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100-500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands in asymmetric catalysis. Isolation and comprehensive characterization of the reaction intermediates support a catalysis cycle proposed by DFT calculations.",

author = "Yury Lebedev and Iuliia Polishchuk and Bholanath Maity and {Dinis Veloso Guerreiro}, Miguel 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 support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.",

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AU - Lebedev, Yury

AU - Polishchuk, Iuliia

AU - Maity, Bholanath

AU - Dinis Veloso Guerreiro, Miguel

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 support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.

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Y1 - 2019/11/8

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AB - A series of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100-500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands in asymmetric catalysis. Isolation and comprehensive characterization of the reaction intermediates support a catalysis cycle proposed by DFT calculations.

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JO - Journal of the American Chemical Society

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Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.

Abstract

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CCDC 1888987: Experimental Crystal Structure Determination : bis(mu-3,3'-bis[3,5-bis(trifluoromethyl)phenyl][1,1'-binaphthalene]-2,2'-diolato)-dimethyl-di-aluminium n-pentane solvate

CCDC 1888986: Experimental Crystal Structure Determination : 3',4,4,5,5-pentamethyl-2H,3'H-spiro[1,3,2-dioxaborolane-2,1'-[1,3,2]oxazaborolo[3,4-a]pyridine]

CCDC 1888988: Experimental Crystal Structure Determination : {3,3'-bis[3,5-bis(trifluoromethyl)phenyl][1,1'-binaphthalene]-2,2'-diolato}-[1-(4-methylphenyl)-1-(pyridin-2-yl)ethan-1-olato]-tetrahydrofuran-aluminium dichloromethane solvate

Cite this

Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1888987: Experimental Crystal Structure Determination : bis(mu-3,3'-bis[3,5-bis(trifluoromethyl)phenyl][1,1'-binaphthalene]-2,2'-diolato)-dimethyl-di-aluminium n-pentane solvate

CCDC 1888986: Experimental Crystal Structure Determination : 3',4,4,5,5-pentamethyl-2H,3'H-spiro[1,3,2-dioxaborolane-2,1'-[1,3,2]oxazaborolo[3,4-a]pyridine]

CCDC 1888988: Experimental Crystal Structure Determination : {3,3'-bis[3,5-bis(trifluoromethyl)phenyl][1,1'-binaphthalene]-2,2'-diolato}-[1-(4-methylphenyl)-1-(pyridin-2-yl)ethan-1-olato]-tetrahydrofuran-aluminium dichloromethane solvate

Cite this