Organocatalytic Tunable Amino Acid Polymers Prepared by Controlled Radical Polymerization

Amanda C. Evans, Annhelen Lu, Courtney Ondeck, Deborah A. Longbottom, Rachel K. O'Reilly

Research output: Contribution to journalArticlepeer-review

53 Citations (Scopus)


Two families of organocatalytically active polystyrene-based copolymers with tunable incorporations of 4-hydroxyproline have been synthesized using two different controlled radical polymerization technologies: nitroxide-mediated polymerization (NMP) and reversible addition−fragmentation chain transfer (RAFT) polymerization. Both of these methodologies allow ready access to a number of polymeric species with controllable molecular weights, narrow molecular weight distributions (ca. 1.2), and reliable functionality incorporations (between 3 and 26%). The organocatalytic activity and selectivity of the NMP-derived family of copolymers with variable incorporations of l-proline have been investigated using the aldol reaction, which provided high conversion to products (>95%) with very good diastereo- and enantioselectivities. We propose that these materials have potential as highly efficient recoverable organocatalyst supports whose solubility and loading can be readily tailored to the desired application.
Original languageEnglish
Pages (from-to)6374-6380
Issue number15
Publication statusPublished - 9 Jul 2010


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