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