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Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction

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    Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction
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    Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290
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    Cite this: Org. Lett. 2004, 6, 1, 131–133
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    https://doi.org/10.1021/ol036219a
    Published November 27, 2003
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    Abstract

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    Chiral nonsymmetric 1,2-diboron adducts are generated by catalytic enantioselective diboration. Oxidation of these adducts provides 1,2-diols in good yield. Alternatively, 1,2-diboron compounds may be reacted, in situ, with aryl halides wherein the less hindered C−B bond participates in cross-coupling. The remaining C−B bond is then oxidized in the reaction workup thereby allowing for net asymmetric carbohydroxylation of alkenes in a tandem one-pot diboration/Suzuki coupling/oxidation sequence.

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    Cite this: Org. Lett. 2004, 6, 1, 131–133
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    https://doi.org/10.1021/ol036219a
    Published November 27, 2003
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