Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2 '-dicarboxamides
Clayden, J., Westlund, N., Frampton, C.S. and Helliwell, M. (2006) Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2 '-dicarboxamides. Organic & Biomolecular Chemistry, 4, (3), 455-461. (doi:10.1039/b514561a).
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Description/Abstract
Addition of laterally lithiated tertiary aromatic amides to benzaldimines controls the formation of a new stereogenic centre adjacent to the benzaldimine aromatic ring. Drawing on the fact that such amino-substituted stereogenic centres may themselves control the conformation of amides, with amido-substituted benzaldimines we found it becomes possible to relay stereochemistry from one amide to another via this intervening stereogenic Centre. A group of dihydrostilbene-2,2'-dicarboxamide derivatives bearing one or two stereogenic axes are made by this method, which demonstrates the use of combined kinetic and thermodynamic control for the relay of stereochemical information.
| Item Type: | Article |
|---|---|
| ISSNs: | 1477-0520 (print) |
| Related URLs: | |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 44406 |
| Date Deposited: | 06 Mar 2007 |
| Last Modified: | 12 Jul 2012 12:42 |
| Contributors: | Clayden, J. (Author) Westlund, N. (Author) Frampton, C.S. (Author) Helliwell, M. (Author) |
| Date: | 2006 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/44406 |
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