Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes

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Abstract: Vinyl boron ate complexes of enantioenriched secondary alkyl pinacolboronic esters undergo stereospecific radical‐induced 1,2‐migration in radical polar crossover reactions. In this three‐component process various commercially available alkyl iodides act as radical precursors and light is used for chain initiation. Subsequent oxidation and protodeborylation leads to valuable α‐chiral ketones and chiral alkanes, respectively, with excellent enantiopurity.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes ; volume:57 ; number:9 ; year:2018 ; pages:2441-2444 ; extent:4
Angewandte Chemie / International edition. International edition ; 57, Heft 9 (2018), 2441-2444 (gesamt 4)

Creator: Gerleve, Carolin
Kischkewitz, Marvin
Studer, Armido

DOI: 10.1002/anie.201711390

URN: urn:nbn:de:101:1-2022090108174798209177

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:38 AM CEST

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Gerleve, Carolin
Kischkewitz, Marvin
Studer, Armido

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Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes

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Other Objects (12)

Boron–Ate Complexes as Chiral Nucleophiles for Asymmetric Synthesis

Asymmetric Copper Hydride Catalyzed Coupling Reaction to Access Chiral Ketones

Synthesis of Axially Chiral Vinyl Arenes by Palladium(0) Catalysis

Manganese Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using Chiral Oxamide Ligands

Anisotropy Factor Spectra for Weakly Allowed Electronic Transitions in Chiral Ketones

Activating Ketones with Low Catalyst Loadings of a Potent Chiral Lewis Acid

Determination of the Absolute Configurations of Chiral Alkanes – An Analysis of the Available Tools

C−N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α‐Oxytosylation of Ketones

“Chiral” and “non-chiral” 3d Seiberg duality

Chiral perturbation theory for nonzero chiral imbalance

Chiral squaring

Chiral magnetoacoustics

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Asymmetric Copper Hydride Catalyzed Coupling Reaction to Access Chiral Ketones

Synthesis of Axially Chiral Vinyl Arenes by Palladium(0) Catalysis

Manganese Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using Chiral Oxamide Ligands

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Activating Ketones with Low Catalyst Loadings of a Potent Chiral Lewis Acid

Determination of the Absolute Configurations of Chiral Alkanes – An Analysis of the Available Tools

C−N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α‐Oxytosylation of Ketones

“Chiral” and “non-chiral” 3d Seiberg duality

Chiral perturbation theory for nonzero chiral imbalance

Chiral squaring

Chiral magnetoacoustics

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Asymmetric Copper Hydride Catalyzed Coupling Reaction to Access Chiral Ketones

Synthesis of Axially Chiral Vinyl Arenes by Palladium(0) Catalysis

Manganese Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using Chiral Oxamide Ligands

Anisotropy Factor Spectra for Weakly Allowed Electronic Transitions in Chiral Ketones

Activating Ketones with Low Catalyst Loadings of a Potent Chiral Lewis Acid

Determination of the Absolute Configurations of Chiral Alkanes – An Analysis of the Available Tools

C−N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α‐Oxytosylation of Ketones

“Chiral” and “non-chiral” 3d Seiberg duality

Chiral perturbation theory for nonzero chiral imbalance

Chiral squaring

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