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Repetitive Mizoroki‐Heck (MH) coupling polymerization was used to create novel chiral polyureas with cinchona alkaloids in the main chain. Apart from two‐component polycondensation of cinchona urea dimers with diiodobenzene via MH reaction conditions, some chiral polyureas were easily polymerized under self polycondensation to yield the chiral polymers. The asymmetric Michael addition reaction was successfully carried out using chiral polymers derived cinchona urea. Interestingly, phenolic‐based chiral polymers served as heterogeneous catalysts for the enantioselective Michael reaction, with high catalytic activity and excellent enantioselectivities (up to 99 % ee). These polymeric catalysts were also stable, and they could be recycled and reused. [ABSTRACT FROM AUTHOR]

Chiral polyureas of cinchona alkaloids were synthesized via repetitive Mizoroki‐Heck (MH) coupling reaction. The Pd‐catalyzed polycondensation of cinchona urea dimers 6 and aromatic diiodide 7 afforded the chiral polyureas (P1−P4). The catalytic activity of the chiral polymers was subsequently investigated. The asymmetric Michael addition of ketoesters to nitroolefins was successfully catalyzed by the polymeric organocatalysts (P1−P4) to give the corresponding Michael adducts with high catalytic activities and excellent enantionselectivities (up to >99% ee). The polymeric catalysts were insoluble in commonly used organic solvents. They were easily recovered and reused several times without any loss of the catalytic activity. [ABSTRACT FROM AUTHOR]