Late-Stage Chloride Displacements Enable Access to Peptoids with cis-Inducing Alkylammonium Side Chains

The synthesis of peptoids possessing multiple cis-inducing monomers with alkylammonium side chains is reported, where chloropropyl side chains are diversified on a solid support by late-stage S(N)2 displacements with amines. The conditions were optimized for a wide variety of primary, secondary, and tertiary alkyl amine nucleophiles. We also demonstrated that multiple chloride displacements could be achieved on sequences possessing trans-inducing N-aryl- and N-imino glycine monomers.