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

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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Bibliographic Details
Published in:Chemical science (Cambridge) Vol. 1; no. 42; pp. 9679 - 9683
Main Authors: Feng, Jian-Jun, Xu, Yan, Oestreich, Martin
Format: Journal Article
Language:English
Published: England Royal Society of Chemistry 14-11-2019
Subjects:
Alcohols
Copper
Dienes
Enantiomers
Ketones
Ligands
Online Access:Get full text
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Summary: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. A ligand-controlled diastereodivergent copper-catalyzed borylative coupling between 1,3-dienes and ketones enables the enantioselective synthesis of densely functionalized tertiary homoallylic alcohols.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/c9sc03531a
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc03531a