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

Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2 '-dicarboxamides
Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2 '-dicarboxamides
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.
1477-0520
455-461
Clayden, J.
e00cdd91-5679-4795-9fd2-90c40042ea62
Westlund, N.
67ab5c55-092b-4157-b179-826d15ad0e7e
Frampton, C.S.
aa1223a1-d9ec-440e-9204-1b869659fe82
Helliwell, M.
88b79c4c-3b44-453f-ad8c-b4b785137958
Clayden, J.
e00cdd91-5679-4795-9fd2-90c40042ea62
Westlund, N.
67ab5c55-092b-4157-b179-826d15ad0e7e
Frampton, C.S.
aa1223a1-d9ec-440e-9204-1b869659fe82
Helliwell, M.
88b79c4c-3b44-453f-ad8c-b4b785137958

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).

Record type: Article

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.

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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: 15 Mar 2024 09:03

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Contributors

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

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