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.