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Pt-Catalyzed Enantioselective Diboration of Terminal Alkenes with B2(pin)2

Laura T. Kliman, Scott N. Mlynarski and James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email:

L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 13210-13211.

DOI: 10.1021/ja9047762 (free Supporting Information)

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A Pt-catalyzed enantioselective addition of bis(pinacolato)diboron to various terminal alkenes occurs in the presence of a readily available chiral phosphonite ligand. While oxidation of the intermediate 1,2-bis(boronate) ester provides a chiral 1,2-diol as the reaction product, homologation/oxidation furnishes a chiral 1,4-diol.

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Additional analytical data have revealed that the platinum complex used for this study is more accurately represented by the formula Pt(dba)3 rather than Pt2(dba)3. A ligand loading of 2 eq. relative to platinum results in optimal selectivity and yield.

James P. Morken, September 14, 2009

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Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration

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Key Words

1,2-Diols, Diboration, Hydrogen Peroxide

ID: J48-Y2009-2780