Dynamically resolved peri-substituted 2-formyl naphthamides: a new class of atropisomeric chiral auxiliary

2-Formyl-N, N-dialkylnaphthamides are chiral, atropisomeric compounds, prov ided they are substituted peri to the amide group. They may be obtained as single enantiomers by dynamic resolution on formation of diastereoisomeric aminal derivatives and used as chiral auxiliaries in a new addition/rearran gement strategy. Nucleophilic attack by vinyl anion equivalents in the pres ence of Lewis acids leads atroposelectively to single diastereoisomers of a llylic alcohols, whose derivatives undergo stereospecific [3,3]-sigmatropic rearrangements. Reductive ozonolysis of the rearrangement product returns an enantiomerically pure functionalised alcohol and in principle allows rec overy of the atropisomeric auxiliary. (C) 2000 Published by Elsevier Scienc e Ltd. All rights reserved.