Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.
The Pt-catalyzed enantioselective addition of bis(pinacolato)diboron to simple monosubstituted alkenes is described. This reaction occurs in the presence of a readily available chiral phosphonite ligand and is effective with a variety of terminal alkene substrates. Importantly, the reaction can operate with catalyst loadings of only 1 mol % Pt. While oxidation of the intermediate 1,2-bis(boronate) ester provides the chiral 1,2-diol as the reaction product, the intermediate may also be subjected to homologation/oxidation to furnish a chiral 1,4-diol as the reaction product.
Kliman
Laura T
LT
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Mlynarski
Scott N
SN
Morken
James P
JP
D000475:Alkenes / Q000737:chemistry*; D001895:Boron / Q000737:chemistry*; D002384:Catalysis; D010984:Platinum / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D010984:Platinum; D001895:Boron
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