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Kinetic resolution by lithiation: highly enantioselective synthesis of substituted dihydrobenzoxazines and tetrahydroquinoxalines
- Publication Year :
- 2022
- Publisher :
- Georg Thieme Verlag KG, 2022.
-
Abstract
- Kinetic resolution provided a highly enantioselective method to access a range of 3-aryl-3,4-dihydro-2H-1,4-benzoxazines using n-butyllithium and the chiral ligand sparteine. The enantioenrichment remained high on removing the tert-butoxycarbonyl (Boc) protecting group. The intermediate organolithium undergoes ring opening to an enamine. The kinetic resolution was extended to give enantiomerically enriched substituted 1,2,3,4-tetrahydroquinoxalines and was applied to the synthesis of an analogue of the antibiotic levofloxacin that was screened for its activity against the human pathogen Streptococcus pneumoniae.
Details
- Language :
- English
- ISSN :
- 00397881
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....0c5ca4b916810cc5a4e4336433d5e5cc