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Spontaneous Resolution of Julia-Kocienski Intermediates Facilitates Phase Separation to Produce Z- and E-Monofluoroalkenes
Alternative Title以Julia-Kocienski成烯反应中间体自拆分所促进的液-液相分离来制备顺式和反式单氟烯烃
Zhao YC(赵延川); Jiang FZ(姜範洲); Hu JB(胡金波)
2015
Source PublicationJ. Am. Chem. Soc.
Volume137Issue:15Pages:5199-5203
AbstractThe 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.
Subtype论文
Subject Area氟化学
DOI10.1021/jacs.5b02112
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000353606700054
Citation statistics
Cited Times:22[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39723
Collection中科院有机氟化学重点实验室
Corresponding AuthorHu JB(胡金波)
Affiliation中科院上海有机化学研究所, 有机氟化学重点实验室
Recommended Citation
GB/T 7714
Zhao YC,Jiang FZ,Hu JB. Spontaneous Resolution of Julia-Kocienski Intermediates Facilitates Phase Separation to Produce Z- and E-Monofluoroalkenes[J]. J. Am. Chem. Soc.,2015,137(15):5199-5203.
APA 赵延川,姜範洲,&胡金波.(2015).Spontaneous Resolution of Julia-Kocienski Intermediates Facilitates Phase Separation to Produce Z- and E-Monofluoroalkenes.J. Am. Chem. Soc.,137(15),5199-5203.
MLA 赵延川,et al."Spontaneous Resolution of Julia-Kocienski Intermediates Facilitates Phase Separation to Produce Z- and E-Monofluoroalkenes".J. Am. Chem. Soc. 137.15(2015):5199-5203.
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