Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes

A highly enantioselective Cu-catalyzed borylation of 2-substituted 1,3-dienes is reported. The use of a chiral phosphanamine ligand is essential in achieving high chemo-, regio-, diastereo- and enantioselectivity. It provides access to a variety of homoallylic boronates in consistently high yield an...

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Detalles Bibliográficos
Autores principales: Liu, Yangbin, Fiorito, Daniele, Mazet, Clément
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6001400/
https://www.ncbi.nlm.nih.gov/pubmed/29997884
http://dx.doi.org/10.1039/c8sc01538d
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author Liu, Yangbin
Fiorito, Daniele
Mazet, Clément
author_facet Liu, Yangbin
Fiorito, Daniele
Mazet, Clément
author_sort Liu, Yangbin
collection PubMed
description A highly enantioselective Cu-catalyzed borylation of 2-substituted 1,3-dienes is reported. The use of a chiral phosphanamine ligand is essential in achieving high chemo-, regio-, diastereo- and enantioselectivity. It provides access to a variety of homoallylic boronates in consistently high yield and enantiomeric excess with 2-aryl and 2-heteroaryl 1,3-dienes as well as sterically demanding 2-alkyl 1,3-dienes. Preliminary investigations based on a non-linear effect study point to a mechanism involving more than one metal center.
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spelling pubmed-60014002018-07-11 Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes Liu, Yangbin Fiorito, Daniele Mazet, Clément Chem Sci Chemistry A highly enantioselective Cu-catalyzed borylation of 2-substituted 1,3-dienes is reported. The use of a chiral phosphanamine ligand is essential in achieving high chemo-, regio-, diastereo- and enantioselectivity. It provides access to a variety of homoallylic boronates in consistently high yield and enantiomeric excess with 2-aryl and 2-heteroaryl 1,3-dienes as well as sterically demanding 2-alkyl 1,3-dienes. Preliminary investigations based on a non-linear effect study point to a mechanism involving more than one metal center. Royal Society of Chemistry 2018-05-23 /pmc/articles/PMC6001400/ /pubmed/29997884 http://dx.doi.org/10.1039/c8sc01538d Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Liu, Yangbin
Fiorito, Daniele
Mazet, Clément
Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes
title Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes
title_full Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes
title_fullStr Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes
title_full_unstemmed Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes
title_short Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes
title_sort copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6001400/
https://www.ncbi.nlm.nih.gov/pubmed/29997884
http://dx.doi.org/10.1039/c8sc01538d
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