Issue 19, 2000

Atropisomeric benzamides and naphthamides as chiral auxiliaries

Abstract

Atropisomeric compounds whose chirality resides in a rotationally restricted aryl–CONR2 bond may be employed as chiral auxiliaries. The electron-withdrawing amide group causes problems in the diastereoselective functionalisation of enolates derived from atropisomeric phenyl esters, but a strategy based on atroposelective nucleophilic addition to a chiral aldehyde followed by stereospecific [3,3] sigmatropic rearrangement allows atropisomeric naphthamides to be used as auxiliaries. The auxiliaries are resolved by dynamic resolution during aminal formation using a proline-derived diamine.

Supplementary files

Article information

Article type
Paper
Submitted
13 Jun 2000
Accepted
01 Aug 2000
First published
14 Sep 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3232-3249

Atropisomeric benzamides and naphthamides as chiral auxiliaries

J. Clayden, M. Helliwell, C. McCarthy and N. Westlund, J. Chem. Soc., Perkin Trans. 1, 2000, 3232 DOI: 10.1039/B004682P

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