Diastereoisomeric atropisomers from the addition of lithiated N,N-dialkyl-l-naphthamides to aldehydes

2-Substituted N,N-diethyl or N,N-diisopropyl 1-naphthamides exist as stable atropisomers. When the 2-substituent is a 1-hydroxyalkyl group, the atropisomers are separable diastereoisomers. Synthesis of these compounds by the addition of aldehydes to orholithiated N,N-dialkyl 1-naphthamides proceeds with moderate to good diastereoselectivity in favour of the aR*S* (syn) diastereoisomer.