A series of lithiation-substitution reactions at the α and β positions of N-Boc N-alkyl cyclopropyl amines is reported. The cyclopropane ring is the preferred position for lithiation in the N-ethyl and N-methyl derivatives 6 and 7, but the N-allyl and N-benzyl derivatives 8 and 9 undergo lithiation at the methylene groups. Lithiations at β positions of the cyclopropylamine ring are observed if the α-position is blocked or the β-positions are ...