Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes
Gil, M.V., Román, E., Serrano, J.A., Hursthouse, M.B. and Light, M.E. (2001) Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes. Tetrahedron: Asymmetry, 12, (12), 1673-1675. (doi: 10.1016/S0957-4166(01)00304-4).
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Description/Abstract
The denitrohydrogenation of chiral 4-alkyl-5-glyco-4-nitrocyclohex-1-enes (1 and 3) with tri-n-butyltin hydride and azobisisobutironitrile proceeded in a completely stereoselective way. In each case. the hydrogen atom provided by tri-n-butyltin hydride adds to a free radical intermediate in a trans mode to the adjacent, sterically demanding, sugar side-chain. Attempts to perform denitroalkylation reactions of 1a, 3a or 8 with electron-deficient alkenes yielded only denitrohydrogenated products.
| Item Type: | Article |
|---|---|
| ISSNs: | 0957-4166 (print) |
| Related URLs: | |
| Keywords: | tandem radical cyclization, transfer chain-reaction, aliphatic nitro-groups, electron-transfer, hydrogen, replacement, hydride, 1-benzyl-1,4-dihydronicotinamide, denitration, reagent |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 19496 |
| Date Deposited: | 16 Feb 2006 |
| Last Modified: | 31 May 2011 23:29 |
| Contributors: | Gil, M.V. (Author) Román, E. (Author) Serrano, J.A. (Author) Hursthouse, M.B. (Author) Light, M.E. (Author) |
| Date: | 16 July 2001 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/19496 |
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