An investigation of (R)-(+)-1-(1-naphthyl)ethylimines and (R)-(+)-1-(phenyl)ethylimines as chiral templates in the staudinger reaction

(R)-(+)-1-(1-Naphthyl)ethylimines were found to be moderately better chiral templates in the Staudinger reaction in comparison to (R)-(+)-1-(phenyl)ethylimines. The best diastereoselectivities and yields were obtained with (R)-(+)-1-(1-naphthyl)ethylimines when toluene was used as the solvent. The resulting diastereomeric cis β-lactams were separated by silica gel flash column chromatography or recrystallization.