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Chemoselective One-Pot Synthesis of Functionalized Amino-azaheterocycles Enabled by COware
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    Chemoselective One-Pot Synthesis of Functionalized Amino-azaheterocycles Enabled by COware
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    WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, U.K.
    GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, U.K.
    § GlaxoSmithKline, 1250 South Collegeville Road, Collegeville, Pennsylvania 19426, United States
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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6368–6371
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    https://doi.org/10.1021/acs.orglett.7b03214
    Published November 14, 2017
    Copyright © 2017 American Chemical Society

    Abstract

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    Functionalized bicyclic amino-azaheterocycles are rapidly accessed in a one-pot cross-coupling/reduction sequence enabled by the use of COware. Incompatible reagents are physically separated in a single reaction vessel to effect two chemoselective transformations—Suzuki–Miyaura cross-coupling and heteroarene reduction. The developed method allows access to novel heterocyclic templates, including semisaturated Hedgehog and dual PI3K/mTOR inhibitors, which show enhanced physicochemical properties compared to their unsaturated counterparts.

    Copyright © 2017 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b03214.

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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6368–6371
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b03214
    Published November 14, 2017
    Copyright © 2017 American Chemical Society

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