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(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.
Cho
Hee Yeon
HY
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Morken
James P
JP
D000447:Aldehydes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D001896:Boron Compounds; D009532:Nickel