Chinese Journal of Organic Chemistry >
Application of Bifunctional Thiourea Catalyst in One Pot Preparation of Polypeptides and Cyclic Carbonates
Received date: 2024-05-24
Revised date: 2024-08-06
Online published: 2024-09-02
Supported by
Hangzhou Normal University(KFJJ2023005)
A series of bifunctional thiourea catalysts were designed and synthesized to catalyze the ring-opening polymerization (ROP) of α-amino acid N-carboxyanhydrides (NCA) for preparation of polypeptides. At the same time, the released carbon dioxide (CO2) during the reaction was fixed and converted into cyclic carbonates with industrial value. One-pot synthesis of well-defined polyesters and cyclic carbonates in high yields was successfully realized by this tandem process, which increased the atomic utilization. We disclosed that this tandem reaction was processed in the presence of propylene oxide (PO), which was not only judiciously added as an in situ activator for the efficient ROP of NCA, but also reacted with CO2 in the next step to form cyclic carbonates. By exploring the effect of different structures of bifunctional thiourea catalysts and reaction conditions on the reaction activity, the reaction efficiency could be highly improved. This tandem process offered unprecedented opportunities for the atom-efficient production of two relevant compounds.
Kaiyue Wang , Mingnuo Xu , Bo Li , Guangpeng Wu . Application of Bifunctional Thiourea Catalyst in One Pot Preparation of Polypeptides and Cyclic Carbonates[J]. Chinese Journal of Organic Chemistry, 2024 , 44(10) : 3206 -3212 . DOI: 10.6023/cjoc202405031
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