Enantioselective aza-Michael Cyclization Reaction Catalyzed by Quinine-Derived Monoquaternary Ammonium Salts: an Effective Route to Synthesize Letermovir
| Autor: | Liang Chen, Wei-Yuan Liu, Si-Ju Bi, Ting Zhou, Jing Pan, Xun-Lei Lv, Kuai-Le Lin, Wei-Cheng Zhou |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Pharmaceutical Fronts, Vol 03, Iss 04, Pp e194-e199 (2021) |
| Druh dokumentu: | article |
| ISSN: | 2628-5088 2628-5096 |
| DOI: | 10.1055/s-0041-1740944 |
| Popis: | Abstract A series of mono- or bis-quaternary ammonium salts derived from cinchonidine or quinine was synthesized and screened as potent phase-transfer catalysts for the reaction of aza-Michael cyclization, the key step in the synthesis of letermovir. During the reaction of aza-Michael cyclization, the screened monoquaternary ammonium salt quinine derivative Q1 transferred 7 to 8 with 91.9% yield and 58% ee. The application of Q1 was preferred, due to its enantioselectivity, the possibility of reuse, and the lower cost in large-scale preparation. Furthermore, the racemization condition of letermovir enantiomer was also explored for the possibility to develop the resolution/racemization process. With the optimal catalyst Q1 in hand, the synthesis of letermovir may be more convenient and economical in the future. |
| Databáze: | Directory of Open Access Journals |
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