Atropisomeric benzamides and naphthamides as chiral auxiliaries

Jonathan Clayden, Madeleine Helliwell*, Catherine McCarthy, Neil Westlund

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

41 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)3232-3249
Number of pages18
JournalPerkin 1
Issue number19
Publication statusPublished - 14 Sep 2000


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