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Spontaneous resolution of Julia-Kocienski intermediates facilitates phase separation to produce Z- and E-monofluoroalkenes.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2015 Apr 22; Vol. 137 (15), pp. 5199-203. Date of Electronic Publication: 2015 Apr 08. - Publication Year :
- 2015
-
Abstract
- The monofluoroalkene motif is important in drug development as it serves as a peptide bond isostere and is found in a number of biologically active compounds with various pharmacological activities. Direct olefination of carbonyl compound is a straightforward way to prepare monofluoroalkenes; however, these methods often result in a mixture of Z- and E-isomers that cannot be easily separated. We discovered a unique spontaneous resolving reaction that simultaneously addresses the problems in the synthesis and separation of Z- and E-monofluoroalkenes. The reaction is accompanied by a highly efficient spontaneous kinetic resolution and phase labeling of monofluoroalkene precursors which allows the separation of Z- and E-monofluoroalkenes by liquid-liquid extraction. The application of the method is demonstrated by the synthesis and separation of potential anticancer agents, which are inseparable by HPLC.
- Subjects :
- Alkenes chemistry
Chromatography, High Pressure Liquid
Hydrocarbons, Fluorinated chemistry
Kinetics
Liquid-Liquid Extraction
Molecular Structure
Stereoisomerism
Alkenes chemical synthesis
Alkenes isolation & purification
Hydrocarbons, Fluorinated chemical synthesis
Hydrocarbons, Fluorinated isolation & purification
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 137
- Issue :
- 15
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 25831969
- Full Text :
- https://doi.org/10.1021/jacs.5b02112