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Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2 '-dicarboxamides

Record type: Article

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.

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Citation

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 and Biomolecular Chemistry, 4, (3), pp. 455-461. (doi:10.1039/b514561a).

More information

Published date: 2006

Identifiers

Local EPrints ID: 44406
URI: http://eprints.soton.ac.uk/id/eprint/44406
ISSN: 1477-0520
PURE UUID: c4c6d2bd-c8bf-467e-9ef6-dbd502fc7557

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Date deposited: 06 Mar 2007
Last modified: 17 Jul 2017 15:14

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Contributors

Author: J. Clayden
Author: N. Westlund
Author: C.S. Frampton
Author: M. Helliwell

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