Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration.
Asymmetric 1,4-dihydroxylations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B(2)(pin)(2)) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyclic substrates will participate in this reaction; however, dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway. In addition to oxidation to the derived 2-buten-1,4-diol, stereoselective carbonyl allylation with the intermediate bis(boronate) ester is also described.
Burks
Heather E
HE
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Kliman
Laura T
LT
Morken
James P
JP
D000466:Alkadienes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D010984:Platinum / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D001896:Boron Compounds; D002074:Butanones; C463639:bis(pinacolato)diboron; D010984:Platinum