Ni-Catalyzed Borylative Diene−Aldehyde Coupling: The Remarkable Effect of P(SiMe3)3

The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. In the presence of P(SiMe3)3, this reductive coupling furnishes allyl boronic esters which are regioisomeric to those obtained w...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 132; no. 22; pp. 7576 - 7577
Main Authors Cho, Hee Yeon, Morken, James P
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 09.06.2010
Subjects
Aldehydes - chemistry
Boron Compounds - chemistry
Catalysis
Nickel - chemistry
Stereoisomerism
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Summary:The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. In the presence of P(SiMe3)3, this reductive coupling furnishes allyl boronic esters which are regioisomeric to those obtained with PCy3 as the ligand. The coupling product may be subject to oxidation, which furnishes the derived 1,3-diol, or allylation with an additional aldehyde, which furnishes the derived 1,6-diol in a stereoselective fashion.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja101513d