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Ireland-Claisen rearrangement of ynamides: stereocontrolled synthesis of 2-amidodienes


Reference:

Heffernan, S.J. and Carbery, D.R., 2012. Ireland-Claisen rearrangement of ynamides: stereocontrolled synthesis of 2-amidodienes. Tetrahedron Letters, 53 (38), p. 5180.

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    Official URL:

    http://dx.doi.org/10.1016/j.tetlet.2012.07.088

    Abstract

    The Ireland-Claisen rearrangement of propargyl ynamido ester substrates is reported. The expected allenamide carboxylic acid products from [3,3]-sigmatropic rearrangement are not isolated, with 2-amidodienes alternatively formed in good yield with high levels of stereocontrol after decarboxylation.

    Details

    Item Type Articles
    CreatorsHeffernan, S.J.and Carbery, D.R.
    DOI10.1016/j.tetlet.2012.07.088
    DepartmentsFaculty of Science > Chemistry
    Publisher StatementCarbery_Tet_Lett_2012_53_38_5180.pdf: NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, vol 53, issue 38, 2012, DOI 10.1016/j.tetlet.2012.07.088
    RefereedYes
    StatusPublished
    ID Code31159

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