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Henry Reaction to Construct Fluorinated Quaternary Carbon Center

Author: HuHuaWei
Tutor: HuangYanGen；GuoYong
School: Donghua University
Course: Applied Chemistry
Keywords: Henry Reaction Fluorine Of quaternary carbons Center fluoride Asymmetric catalyst
CLC: O621.25
Type: Master's thesis
Year: 2012
Downloads: 8
Quote: 0
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Abstract


The Henry reaction called Nitroaldol reaction is a basic carbon - carbon bond formation reaction , the reaction can be obtained a bifunctional compound having an important role in value -beta - nitro alcohol . Further, since the special effect of the fluorine atoms (relatively small volume , high electrical negative , high fat-soluble) so that the fluorine-containing compound especially a fluorine-containing compound having a physiologically active to receive widespread attention , wherein a compound having a fluorinated quaternary carbon center is one of its focus . First part : This article starting from the halogenated alkane to prepare a series of nitro compounds , and then synthesized with an electrophilic fluorinating reagent of the corresponding α- fluoro nitroalkanes , subsequently investigated them with various aldehydes Henry Reaction to construct a compound having a fluorinated quaternary carbon center . Finally, we derived by single crystal X-ray diffraction analysis of the Henry reaction product 48bf and 48bg , a fluorine atom and a hydroxyl group in the trans- described we mainly obtained mainly in the trans configuration product . The second part : We try to use the C2 symmetry copper - ah oxazoline complexes as catalysts , and look forward to non- enantioselectively build single - fluoro-substituted quaternary carbon center , but the result is not very satisfactory , the yield is very low . When using a large excess (10 equiv.) Fluoro nitroalkane , the reaction can be obtained a good yield and moderate enantioselectivity (51 ? ), But less than ideal so that atom economy .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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