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Kinetic Resolution by Lithiation: Highly Enantioselective Synthesis of Substituted Dihydrobenzoxazines and Tetrahydroquinoxalines.
- Source :
-
Synthesis . 2022, Vol. 54 Issue 2, p355-368. 14p. - Publication Year :
- 2022
-
Abstract
- Kinetic resolution provided a highly enantioselective method to access a range of 3-aryl-3,4-dihydro-2 H -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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00397881
- Volume :
- 54
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Synthesis
- Publication Type :
- Academic Journal
- Accession number :
- 154452104
- Full Text :
- https://doi.org/10.1055/a-1638-2478