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Synthesis of chiral polyurethanes of cinchona alkaloids for the enantioselective synthesis in asymmetric catalysis

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Abstract Chiral polyurethanes of cinchona alkaloid were synthesized via repetitive Mizoroki-Heck (MH) coupling reaction. The Pd-catalyzed polycondensation of cinchona urethane dimers and aromatic diiodides afforded the chiral polyurethanes. The chiral… Click to show full abstract

Abstract Chiral polyurethanes of cinchona alkaloid were synthesized via repetitive Mizoroki-Heck (MH) coupling reaction. The Pd-catalyzed polycondensation of cinchona urethane dimers and aromatic diiodides afforded the chiral polyurethanes. The chiral polyurethane bearing free OH group at the C6’ position of the quinoline ring in the cinchona alkaloid unit showed high catalytic activities and excellent enantioselectivities (up to 97% ee) in the Michael addition reactions.

Keywords: synthesis; cinchona alkaloids; chiral polyurethanes; synthesis chiral; alkaloids enantioselective; polyurethanes cinchona

Journal Title: Catalysis Communications
Year Published: 2019

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