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Asymmetric Synthesis of Anti‐tuberculosis‐specific Drug TBAJ‐876 through Synergistic Li/Li Catalysis.
- Source :
-
Chinese Journal of Chemistry . Jun2023, Vol. 41 Issue 11, p1319-1326. 8p. - Publication Year :
- 2023
-
Abstract
- Comprehensive Summary: TBAJ‐876, developed by TB Alliance, a novel anti‐tuberculosis‐specific drug, has entered Phase II clinical trials. Herein, the first asymmetric synthesis of TBAJ‐876 has been realized using synergistic Li/Li catalysis with excellent yield of 95% and 88 : 12 er (99.6 : 0.4 er, 10 : 1 dr after simple recrystallization). Furthermore, DFT calculations and 7Li‐NMR analysis illustrated the mechanism of the synergistic reaction: a chiral Li‐complex activates the nucleophile to control the stereoselectivity, while the other achiral Li‐complex activates the electrophile to catalyze the carbonyl addition reaction. Additionally, this protocol has been successfully carried out at 5 gram‐scale, showing its industrial potential. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 1001604X
- Volume :
- 41
- Issue :
- 11
- Database :
- Academic Search Index
- Journal :
- Chinese Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 163411134
- Full Text :
- https://doi.org/10.1002/cjoc.202200817