Atropisomeric benzamides and naphthamides as chiral auxiliaries †
Journal of the Chemical Society Perkin Transactions 12000Iss. 19, pp. 3232–3249
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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.
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