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Carbon−Carbon Bond-Forming Enantioselective Synthesis of Chiral Organosilicon Compounds by Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition Reaction
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    Carbon−Carbon Bond-Forming Enantioselective Synthesis of Chiral Organosilicon Compounds by Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition Reaction
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    Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
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    Organic Letters

    Cite this: Org. Lett. 2005, 7, 21, 4757–4759
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    https://doi.org/10.1021/ol051978+
    Published September 22, 2005
    Copyright © 2005 American Chemical Society

    Abstract

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    A new synthetic method for chiral organosilicon compounds through a rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to β-silyl α,β-unsaturated carbonyl compounds has been developed. By employing (R,R)-Bn-bod* as a ligand, a range of arylboronic acids can be coupled with these substrates in very high enantiomeric excess. The resulting β-silyl 1,4-adducts can be converted to β-hydroxy carbonyl compounds or allylsilanes while retaining their stereochemical information.

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    Organic Letters

    Cite this: Org. Lett. 2005, 7, 21, 4757–4759
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol051978+
    Published September 22, 2005
    Copyright © 2005 American Chemical Society

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