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    NH-Isoxazolo-bicycles; new molecular scaffolds for organocatalysis

    Doyle, Linda and Heaney, Frances (2011) NH-Isoxazolo-bicycles; new molecular scaffolds for organocatalysis. Tetrahedron, 67 (11). pp. 2132-2138. ISSN 0040-4020

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    A new scaffold for organocatalysis of the DielseAlder reaction is disclosed; an isoxazolidine ring forms the core of the catalyst and its activity is enhanced by judicious fusion of a second five-membered heterocycle to the c-edge. The catalyst performance is improved by the incorporation of an endo-cyclic electron withdrawing group adjacent to the fusion point. The organic core is effective only in the presence of an acid co-catalyst and whilst the two-component system shows potential as an enantioselective catalyst it is demonstrated that stereocontrol is a feature of the organic core and is fully independent of the choice of co-catalyst.

    Item Type: Article
    Keywords: Organocatalysis; Diels–Alder; Isoxazolofused bicycle; Enantioselectivity;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 4294
    Depositing User: Dr. Frances Heaney
    Date Deposited: 09 Apr 2013 11:25
    Journal or Publication Title: Tetrahedron
    Publisher: Elsevier
    Refereed: Yes
    Use Licence: This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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