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

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 c...

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Detalles Bibliográficos
Autores principales: Gerleve, Carolin, Kischkewitz, Marvin, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838550/
https://www.ncbi.nlm.nih.gov/pubmed/29239507
http://dx.doi.org/10.1002/anie.201711390
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author Gerleve, Carolin
Kischkewitz, Marvin
Studer, Armido
author_facet Gerleve, Carolin
Kischkewitz, Marvin
Studer, Armido
author_sort Gerleve, Carolin
collection PubMed
description 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.
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spelling pubmed-58385502018-03-12 Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes Gerleve, Carolin Kischkewitz, Marvin Studer, Armido Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2018-01-16 2018-02-23 /pmc/articles/PMC5838550/ /pubmed/29239507 http://dx.doi.org/10.1002/anie.201711390 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Gerleve, Carolin
Kischkewitz, Marvin
Studer, Armido
Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes
title Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes
title_full Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes
title_fullStr Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes
title_full_unstemmed Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes
title_short Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes
title_sort synthesis of α‐chiral ketones and chiral alkanes using radical polar crossover reactions of vinyl boron ate complexes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838550/
https://www.ncbi.nlm.nih.gov/pubmed/29239507
http://dx.doi.org/10.1002/anie.201711390
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