Grigg, R., Kilner, C., Sarker, M.A.B., Orgaz de la Cierva, C. and Dondas, H.A. (2008) X=Y–ZH compounds as potential 1,3-dipoles. Part 64: Synthesis of highly substituted conformationally restricted and spiro nitropyrrolidines via Ag(I) catalysed azomethine ylide cycloadditions. Tetrahedron, 64 (37). pp. 8974-8991. ISSN 0040-4020
Full text available as:![[img]](http://eprints.whiterose.ac.uk/style/images/fileicons/text.png) |
Text
griggsr2.pdf Download (729Kb) |
Abstract
1,3-Dipolar reactions of imines of both acyclic and cyclic α-amino esters with a range of nitroolefins using a combination of AgOAc or Ag2O with NEt3 are described. In most cases the reactions were highly regio- and stereospecific and endo-cycloadducts were obtained in good yield. However, in a few cases the initially formed cycloadducts underwent base catalysed epimerisation. The stereochemistry of the cycloadducts was assigned from NOE data and established unequivocally in several cases by X-ray crystallography.
| Item Type: | Article |
|---|---|
| Copyright, Publisher and Additional Information: | © 2008 Elsevier B.V This is an author produced version of a paper published in Tetrahedron. Uploaded in accordance with the publisher's self archiving policy. |
| Academic Units: | The University of Leeds > Faculty of Maths and Physical Sciences (Leeds) > School of Chemistry (Leeds) |
| Depositing User: | Sherpa Assistant |
| Date Deposited: | 10 Oct 2008 15:25 |
| Last Modified: | 08 Feb 2013 16:56 |
| Published Version: | http://dx.doi.org/10.1016/j.tet.2008.05.132 |
| Status: | Published |
| Publisher: | Elsevier B.V. |
| Identification Number: | 10.1016/j.tet.2008.05.132 |
| URI: | http://eprints.whiterose.ac.uk/id/eprint/4740 |
Actions (login required)
 |
View Item |
