A multi-component reaction (MCR) approach to the synthesis of highly diverse polymers with polypeptide-like features

Asymmetric Isocyanide‐Based MCRs

“…As for the related Passerini reaction, even the use of aldehydes that are known to give excellent asymmetric induction in the reaction with other kinds of C-nucleophiles, results in low or moderate diastereoisomeric ratios. For example, both norbornyl aldehyde 39 [47] and a-alkoxyaldehyde 40 [3,48] gave drs lower than 2:1 (Scheme 1.16). The same happens with ortho-substituted chromium complex 41 [49], which usually leads to very high asymmetric induction in other nucleophilic additions.…”

Potentially biocompatible polyacrylamides derived by the Ugi four-component reaction

“…The Ugi-4CR further provided a strategy for the efficient conjugation of two types of polymers to either a fluorescent molecule, chemical agent or protein [37,38]. With regard to the monomer synthesis, the Ugi-4CR allowed the preparation of polymers with polypeptide-like features [39], a-amide substituted polyamides [40], convertible polyamides [41], and polyurethanes [42].…”

Synthesis of Diverse Asymmetric α,ω‐Dienes Via the Passerini Three‐Component Reaction for Head‐to‐Tail ADMET Polymerization

“…The application of MCRs in polymer science is a relatively new research area . The first example was described in 2003 by Wright and co‐workers, who employed the Ugi four‐component reaction (Ugi‐4CR) for the synthesis of monomers for ring‐opening metathesis polymerization (ROMP). These monomers were synthesized by reaction of norbornenyl aldehydes and carboxylic acids in combination with an amine and isocyanide, thus leading to macromolecules with polypeptide‐like features.…”