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Tandem Allylation/1,2-Boronate Rearrangement for the Asymmetric Synthesis of Indolines with Adjacent Quaternary Stereocenters

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    Tandem Allylation/1,2-Boronate Rearrangement for the Asymmetric Synthesis of Indolines with Adjacent Quaternary Stereocenters
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    Cite this: J. Am. Chem. Soc. 2018, 140, 41, 13242–13252
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    https://doi.org/10.1021/jacs.8b06629
    Published September 21, 2018
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    Abstract

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    A three-component coupling using lithiated indoles, boronate esters and allylic acetates generates chiral indolines with adjacent quaternary stereocenters. Successful stereocontrol required the use of phosphoramidite ligands not previously described for organopalladium chemistry. Mechanistic studies indicate a monodentate PdL intermediate, and a stepwise allylation-aryl/alkyl migration. A protodeborylation strategy was used to install a C–H bond in place of the C–B bond. A photoredox coupling was used to replace C–B bond with a C–C bond in a highly diastereoselective manner. In the specific case of methyl-vinyl ketone, a novel radical-mediated annulation provides polycyclic products with high enantio- and diastereoselectivity.

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    • Crystal data for compound 12a (CIF)

    • Crystal data for compound 12u (CIF)

    • Crystal data for compound 14a (CIF)

    • Crystal data for compound 14e (CIF)

    • Crystal data for compound 16d (CIF)

    • Crystal data for compound 17 (CIF)

    • Crystal data for compound 19 (CIF)

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    Cite this: J. Am. Chem. Soc. 2018, 140, 41, 13242–13252
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    https://doi.org/10.1021/jacs.8b06629
    Published September 21, 2018
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