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Chemo- and regioselectivity in the reactions between highly electrophilic fluorine containing dicarbonyl compounds and amines. Improved synthesis of the corresponding imines/enamines
Authors:Hironari OhkuraDmitrii O. Berbasov  Vadim A. Soloshonok
Affiliation:Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019, USA
Abstract:Chemo- and regioselectivity in the reactions between highly electrophilic fluorine containing dicarbonyl compounds (ethyl 4,4,4-trifluoroacetoacetate, 3,3,3-trifluoropyruvate and 1,1,1,5,5,5-hexafluoropentane-2,4-dione) and various benzylamines were systematically studied. The results obtained lead to the development of a generalized and practical method for large-scale synthesis of the corresponding imines/enamines, useful starting materials for preparation fluorinated amines and amino acid.
Keywords:chemoselectivity   regioselectivity   nucleophilicity   electrophilicity   enamines   imines   fluorine and compounds
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