Study on enantiomerically pure 2-substituted N,N-dialkyl-1-naphthamides: resolution, absolute stereochemistry, and application to desymmetrization of cyclic meso anhydrides

The axially chiral 2-substituted N,N-diisoproyl-1-1-naphthamides 1 and 2 were resolved by HPLC over a chiral stationary phase to provide enantiomerically pure atropisomers. The absolute stereochemistry of was determined by X-ray crystallographic analysis of the corresponding (1S)-camphanic acid derivative. Desymmetrization of cyclic meso anhydrides 5a and 5b using (-)-syn-1 gave a single diastercomer in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved