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Ni-catalyzed borylative diene-aldehyde coupling: the remarkable effect of P(SiMe3)3.

ABSTRACT: 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(SiMe(3))(3), this reductive coupling furnishes allyl boronic esters which are regioisomeric to those obtained with PCy(3) 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.

SUBMITTER: Cho HY

PROVIDER: S-EPMC2912217 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Ni-catalyzed borylative diene-aldehyde coupling: the remarkable effect of P(SiMe3)3.

Cho Hee Yeon HY Morken James P JP

Journal of the American Chemical Society 20100601 22

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(SiMe(3))(3), this reductive coupling furnishes allyl boronic esters which are regioisomeric to those obtained with PCy(3) 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 ...[more]

PMID: 20481451

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