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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Original Publication URL: http://dx.doi.org/10.1039/b514561a

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
ePrint ID: 44406
Date Deposited: 06 Mar 2007
Last Modified: 27 Mar 2014 18:28
URI: http://eprints.soton.ac.uk/id/eprint/44406

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