The efficiency of enantiomeric 1‐aminoindane and 1,2,3,4‐tetrahydro‐1‐naphthylamine as chiral auxiliaries in trans‐ß‐lactam formation via Staudinger cycloaddition is examined. Aromatic aldehydes possessing one, two, or three methoxyl groups are used as imine precursors, and the influence of their number and position on the reaction output is studied. A comparison with the results obtained from 1‐phenylethyl and 1‐(2‐naphthyl)ethylamine‐derived imines is performed.