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Issue 3, 2006
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Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2′-dicarboxamides

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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.

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

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Article information


Submitted
13 Oct 2005
Accepted
23 Nov 2005
First published
22 Dec 2005

Org. Biomol. Chem., 2006,4, 455-461
Article type
Paper

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

J. Clayden, N. Westlund, C. S. Frampton and M. Helliwell, Org. Biomol. Chem., 2006, 4, 455
DOI: 10.1039/B514561A

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