315668-02-1Relevant articles and documents
Atropisomeric benzamides and naphthamides as chiral auxiliaries
Clayden, Jonathan,Helliwell, Madeleine,McCarthy, Catherine,Westlund, Neil
, p. 3232 - 3249 (2007/10/03)
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. The Royal Society of Chemistry 2000.