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Highly Enantioselective Intermolecular Hydroamination of Allylic Amines with Chiral Aldehydes as Tethering Catalysts

Authors

  • Melissa J. MacDonald,

    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)
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  • Colin R. Hesp,

    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)
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  • Derek J. Schipper,

    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)
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  • Marc Pesant,

    1. Boehringer Ingelheim (Canada) Ltd, 2100 Cunard Street, Laval, QC, H7S 2G5 (Canada)
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  • Prof. André M. Beauchemin

    Corresponding author
    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)
    • Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)
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Abstract

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Chirally LinkedIn: Chiral aldehydes are effective tethering catalysts for enantioselective intermolecular hydroamination, which provides access to vicinal diamine motifs in good yields and excellent enantioselectivities (see scheme). This work highlights simple chiral α-oxygenated aldehydes as effective organocatalysts capable of efficiently inducing asymmetry through transient intramolecularity.

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