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...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 132; no. 22; pp. 7576 - 7578
Main Authors Cho, Hee Yeon, Morken, James P.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 09.06.2010
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
REARRANGEMENT
ALCOHOLS
PHOSPHORUS
MECHANISM
ZEROVALENT NICKEL-COMPLEX
1,3-DIENE
STEREOSELECTIVE-SYNTHESIS
ASYMMETRIC CYCLIZATION
HOMOALLYLATION
DERIVATIVES
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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 allytation with an additional aldehyde, which furnishes the derived 1,6-diol in a stereoselective fashion.
Bibliography:NIH RePORTER
ISSN:0002-7863
DOI:10.1021/ja101513d