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Brown, Jack A., Chudasama , Vijay, Giles, Melvyn E., Gill, Duncan M., Keegan, Phillip S., Kerr, William J., Munday , Rachel, Griffin, Karen and Watts, Andrew (2012) E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates. Organic & Biomolecular Chemistry, 10 (3). pp. 509-511. ISSN 1477-0520
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Official URL: http://dx.doi.org/10.1039/C1OB06569F
DOI: 10.1039/C1OB06569F
Abstract
Treatment of glycidyl sulfonamides with LDA delivers the corresponding enesulfonamide with good selectivity for the E-isomer, whereas the corresponding carbamates exhibit selectivity for the Z-enecarbamate. An E1cB elimination mechanism proceeding from a substrate–base chelate complex is advanced as rationalisation of the latter set of Z-selective outcomes.
| Item Type: | Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Schools: | School of Applied Sciences |
| Depositing User: | Duncan Gill |
| Date Deposited: | 01 Jun 2012 10:03 |
| Last Modified: | 17 Oct 2012 12:07 |
| URI: | http://eprints.hud.ac.uk/id/eprint/13354 |
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