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Research of Ireland-Claisen Rearrangement of Butenyl Trifluoroacetate and Asymmetric Syntheses of α-fluoro-β-amino Acids
Author: JingZhiTao
Tutor: QingFengZuo
School: Donghua University
Course: Organic Chemistry
Keywords: Ireland-Claisen rearrangement α- fluoro -β- amino acid Reformatsky reaction
CLC: O621.34
Type: Master's thesis
Year: 2010
Downloads: 29
Quote: 0
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Abstract
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Known in some bioactive molecule to introducing fluorine atomic better biological activity, so the development of organic molecules can be introduced into the fluorine atoms of synthetic strategy has become a huge challenge. Paper is divided into two parts: The first part : difluoromethylene containing organic compounds due to their unique biological activity, has become a very important target molecules in organic synthesis . Therefore, we would like to use (Z) -2,2,2 - trifluoro - acetic acid - 4' -benzyloxy- 2' - butenyl ester 2 catalyzed by magnesium Ireland-Claisen rearrangement to introduce difluoromethylene . After a lot of attempts by 19F NMR detection , we have always failed to detect difluoro enol ether intermediate formation. Compound 2 may be due to its effect in the weak electron-withdrawing . Part II : In recent years , the fluorinated -β- amino acids have become the pharmaceutical and biochemical research focus and has made a lot of research. We imide with tert -butyl group as a chiral auxiliary , with a single bromine fluoride of ethyl acetate and tert -butyl sulfonamide To a THF solution of the active zinc Reformatsky reaction occurs in good yield ( 70-86 % ) and moderate stereoselectivity ( 66:34-92:8 ) , synthesized a series of α- fluoro -β- amino acid derivative . Off by acid hydrolysis and then all of the protecting groups in ( 70-93 % ) yield of the corresponding α- fluoro -β- amino acids.
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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Synthetic organic chemistry > Asymmetric Organic Synthesis
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