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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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.
|Digital Object Identifier (DOI):||doi:10.1039/b514561a|
Q Science > QD Chemistry
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|Date Deposited:||06 Mar 2007|
|Last Modified:||06 Aug 2015 02:37|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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