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  • A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control

    Author(s)
    Broustal, Garance
    Ariza, Xavier
    Campagne, Jean-Marc
    Garcia, Jordi
    Georges, Yohan
    Marinetti, Angela
    Robiette, Raphaël
    Griffith University Author(s)
    Broustal, Garance RJ.
    Year published
    2007
    Metadata
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    Abstract
    Direct enantiocontrolled access to 1,3-amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama-aldol addition). The obtained -hydroxyesters were reduced to pent-2-ene-1,5-diols, which were converted into the corresponding dicarbamates with tosyl isocyanate. Stereoselective cyclization of these dicarbamates proceeded with 1,3-asymmetric induction under either thermodynamic or kinetic control to afford enantioselectively six-membered-ring cyclic carbamates. Calculations enabled us to ...
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    Direct enantiocontrolled access to 1,3-amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama-aldol addition). The obtained -hydroxyesters were reduced to pent-2-ene-1,5-diols, which were converted into the corresponding dicarbamates with tosyl isocyanate. Stereoselective cyclization of these dicarbamates proceeded with 1,3-asymmetric induction under either thermodynamic or kinetic control to afford enantioselectively six-membered-ring cyclic carbamates. Calculations enabled us to rationalize the observed stereoselectivity.
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    Journal Title
    European Journal of Organic Chemistry
    Volume
    2007
    Issue
    26
    DOI
    https://doi.org/10.1002/ejoc.200700503
    Subject
    Medicinal and Biomolecular Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/27137
    Collection
    • Journal articles

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