Late-Stage Chloride Displacements Enable Access to Peptoids with cis-Inducing Alkylammonium Side Chains.
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ABSTRACT:
SUBMITTER: Davern CM
PROVIDER: S-EPMC10903636 | biostudies-literature | 2023 Aug
REPOSITORIES: biostudies-literature
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Late-Stage Chloride Displacements Enable Access to Peptoids with <i>cis</i>-Inducing Alkylammonium Side Chains.
Davern Carolynn M CM Proulx Caroline C
Organic letters 20230814 33
The synthesis of peptoids possessing multiple <i>cis</i>-inducing monomers with alkylammonium side chains is reported, where chloropropyl side chains are diversified on a solid support by late-stage S<sub>N</sub>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 <i>trans</i>-inducing <i>N</i>-aryl- and <i>N</i ...[more]
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