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    Hydroamidation of Vinyl Ethers by Acid-Catalyzed Multicomponent Isocyanide Addition

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    Brock_Carlson_Brenden_2021.pdf
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    Author
    Carlson, Brenden Matthew
    Keyword
    isocyanide
    enol ether
    glycal sugar
    hydroamidation
    Passerini-like
    
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    URI
    http://hdl.handle.net/10464/15055
    Abstract
    Hydroamidation of carbon–carbon double bonds is an attractive strategy for installing nitrogen functionality into molecular scaffolds and, with it, increasing molecular complexity. To date, metal-based approaches have dominated this area of chemical synthesis despite the drawbacks of air and moisture sensitivity, limited functional group tolerance, toxicity, and/or high cost often associated with using metals. Herein is enclosed an operationally simple, metal-free, one-pot, regioselective, multicomponent synthetic procedure for the hydroamidation of carbon–carbon double bonds. This method features mild reaction conditions and utilizes isocyanides and vinyl ethers for the rapid and modular synthesis of α-oxygenated amide scaffolds. Additional effort was put towards synthesizing reactive natural products as substrates to the developed methodology, and drafting a probable catalytic cycle for the main and side reactions present within this multicomponent procedure.
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