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Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines

A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, conve...

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Detalles Bibliográficos
Autores principales: Rae, James, Yeung, Kay, McDouall, Joseph J. W., Procter, David J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4736445/
https://www.ncbi.nlm.nih.gov/pubmed/26632675
http://dx.doi.org/10.1002/anie.201508959
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author Rae, James
Yeung, Kay
McDouall, Joseph J. W.
Procter, David J.
author_facet Rae, James
Yeung, Kay
McDouall, Joseph J. W.
Procter, David J.
author_sort Rae, James
collection PubMed
description A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α‐substituted‐β‐amino ketones. A computational study has been used to probe the stereochemical course of the cross‐coupling.
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spelling pubmed-47364452016-07-08 Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines Rae, James Yeung, Kay McDouall, Joseph J. W. Procter, David J. Angew Chem Int Ed Engl Communications A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α‐substituted‐β‐amino ketones. A computational study has been used to probe the stereochemical course of the cross‐coupling. John Wiley and Sons Inc. 2015-12-03 2016-01-18 /pmc/articles/PMC4736445/ /pubmed/26632675 http://dx.doi.org/10.1002/anie.201508959 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Rae, James
Yeung, Kay
McDouall, Joseph J. W.
Procter, David J.
Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
title Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
title_full Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
title_fullStr Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
title_full_unstemmed Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
title_short Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
title_sort copper‐catalyzed borylative cross‐coupling of allenes and imines: selective three‐component assembly of branched homoallyl amines
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4736445/
https://www.ncbi.nlm.nih.gov/pubmed/26632675
http://dx.doi.org/10.1002/anie.201508959
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