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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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Abstract
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 |
| Related URLs: | |
| URI: | https://mural.maynoothuniversity.ie/id/eprint/4294 |
| 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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