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Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.

ABSTRACT: 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.

SUBMITTER: Kliman LT

PROVIDER: S-EPMC2763309 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.

Kliman Laura T LT Mlynarski Scott N SN Morken James P JP

Journal of the American Chemical Society 20090901 37

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 ...[more]

PMID: 19702329

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