Catalytic Enantioselective Functionalization of Maleimides: An Update

• Published in: Chinese journal of chemistry 2024-12, Vol.42 (24), p.3605-3622
• Main Authors: Amatore, Muriel, Bonne, Damien, Constantieux, Thierry, Rodriguez, Jean
• Format: Article
• Language: English
• Subjects: Addition polymerization; Additions; Chirality; Cycloadditions; Domino reactions; Enantiomers; Enantioselective catalysis; Heterocycles; Intermediates; Maleimides; Natural products; Polymers
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.202400787

Comprehensive Summary Maleimide derivatives are well‐established reactive intermediates also found in natural products, synthetic pharmaceuticals and functional polymers. Their specific reactivity found widespread applications in the field of bioconjugation and allowed for the development of highly selective functionalizations based on simple additions and cycloadditions with the possible control of central and C–N axial chirality. These multisite‐reactive scaffolds have aroused a long‐standing interest throughout the scientific community more particularly as powerful electrophilic partners and more recently as nucleophilic partners in some specific transformations. The persistent interest in these easily accessible synthetic platforms over the last decade has enabled the development of new enantioselective transformations and the major advancements in this field are presented in this review. Key Scientists Maleimides are multisite‐reactive scaffolds that have stimulated a growing interest in the field of synthetic organic chemistry. The present review covers the utilization of maleimides as electrophilic partners and pro‐nucleophilic partners in metal‐catalyzed or organocatalyzed functionalizations with the control of either central and/or axial chirality.