Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones

A copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and ketones allows for the chemo-, regio-, diastereo- and enantioselective assembly of densely functionalized tertiary homoallylic alcohols. The relative configuration of the vicinal stereocenters is controlled by the...

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Detalles Bibliográficos
Autores principales: Feng, Jian-Jun, Xu, Yan, Oestreich, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6977547/
https://www.ncbi.nlm.nih.gov/pubmed/32015801
http://dx.doi.org/10.1039/c9sc03531a
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author Feng, Jian-Jun
Xu, Yan
Oestreich, Martin
author_facet Feng, Jian-Jun
Xu, Yan
Oestreich, Martin
author_sort Feng, Jian-Jun
collection PubMed
description A copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and ketones allows for the chemo-, regio-, diastereo- and enantioselective assembly of densely functionalized tertiary homoallylic alcohols. The relative configuration of the vicinal stereocenters is controlled by the chiral ligand employed. Subsequent transformations illustrate the versatility of these valuable chiral building blocks.
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spelling pubmed-69775472020-02-03 Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones Feng, Jian-Jun Xu, Yan Oestreich, Martin Chem Sci Chemistry A copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and ketones allows for the chemo-, regio-, diastereo- and enantioselective assembly of densely functionalized tertiary homoallylic alcohols. The relative configuration of the vicinal stereocenters is controlled by the chiral ligand employed. Subsequent transformations illustrate the versatility of these valuable chiral building blocks. Royal Society of Chemistry 2019-08-20 /pmc/articles/PMC6977547/ /pubmed/32015801 http://dx.doi.org/10.1039/c9sc03531a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Feng, Jian-Jun
Xu, Yan
Oestreich, Martin
Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones
title Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones
title_full Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones
title_fullStr Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones
title_full_unstemmed Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones
title_short Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones
title_sort ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6977547/
https://www.ncbi.nlm.nih.gov/pubmed/32015801
http://dx.doi.org/10.1039/c9sc03531a
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AT oestreichmartin ligandcontrolleddiastereodivergentenantioandregioselectivecoppercatalyzedhydroxyalkylborationof13dieneswithketones

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