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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Published inChemical science (Cambridge) Vol. 1; no. 42; pp. 9679 - 9683
Main Authors Feng, Jian-Jun, Xu, Yan, Oestreich, Martin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.11.2019
Royal Society of Chemistry
Subjects
Alcohols
Chemistry
Chemistry, Multidisciplinary
Copper
Dienes
Enantiomers
Ketones
Ligands
Physical Sciences
Science & Technology
DIENES
TERTIARY ALCOHOLS
REAGENTS
COUPLING REACTIONS
ALLYLBORATION
HYDROHYDROXYALKYLATION
CARBONYL ALLYLATION
ASYMMETRIC ADDITION
ALDEHYDES
ENANTIOSELECTIVE ADDITION
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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
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SourceType-Scholarly Journals-1
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These authors contributed equally.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc03531a