170804-10-1Relevant academic research and scientific papers
A Domino Azidation/C-H Amination Approach toward Trifluoromethyl Substituted Imidazoles
Ma, Haichao,Zhang, Xiaoyan,Chen, Liangliang,Yu, Wei
, p. 11841 - 11847 (2017)
N-Alkyl enamines can be transformed into 2,4,5-trisubsituted imidazoles by reacting with (diacetoxyiodo)benzene and TMSN3 under the catalysis of a copper salt such as Cu(OAc)2. Tetrabutyl ammonium iodide was also capable of promoting the reaction. The transformation from N-alkyl enamines into 2,4,5-trisubsituted imidazoles took place in a domino azidation/intramolecular C(sp3)-H amination pattern. The present reaction provides a new efficient method for the preparation of 4-(trifluoromethyl) imidazoles.
Ethyl-4,4,4-trifluoroacetoacetate (ETFAA), a powerful building block for enantiopure chirons in trifluoromethyl-β-amino acid series
Michaut, Valérie,Metz, Fran?ois,Paris, Jean-Marc,Plaquevent, Jean-Christophe
, p. 889 - 895 (2008/03/14)
Herein are studied new transformations of ethyl-4,4,4-trifluoroacetoacetate (ETFAA), giving access to a series of enantiopure chirons bearing both a trifluoromethyl group and an amino moiety. The key intermediate is obtained optically pure by a resolution
Enantioselective organocatalytic route to trifluoromethyl-β-amino acids using chiral bases
Michaut, Valérie,Metz, Fran?ois,Paris, Jean-Marc,Plaquevent, Jean-Christophe
, p. 500 - 506 (2008/01/03)
Herein are studied new aspects of enantioselective (1,3) proton transfer of ethyl-4,4,4-trifluoroacetoacetate (ETFAA) amino derivatives. When catalyzed by an appropriate chiral base, ee's as high as 71% are observed. Special emphasis is given to mechanist
Chemo- and regioselectivity in the reactions between highly electrophilic fluorine containing dicarbonyl compounds and amines. Improved synthesis of the corresponding imines/enamines
Ohkura, Hironari,Berbasov, Dmitrii O.,Soloshonok, Vadim A.
, p. 1647 - 1656 (2007/10/03)
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.
Easy synthesis of (E)- or (Z)-perfluorinated β-enaminaoesters
Prié, Gildas,Richard, Sébastien,Parrain, Jean-Luc,Duchêne, Alain,Abarbri, Mohamed
, p. 35 - 41 (2007/10/03)
(E)- or (Z)-perfluorinated β-enaminoesters were prepared by direct addition of primary or secondary amines to ethyl perfluoroalkynoates without any catalyst.
A convenient synthesis of perfluoroalkylated enamines and vinyl phosphonates
Cen, Wenbiao,Ni, Yuhua,Shen, Yanchang
, p. 161 - 164 (2007/10/02)
The reaction of fluoroalkynes with ammonia and benzylamine gave perfluoroalkylated enamines predominantly as the Z isomer, which were hydrogenated with palladium on carbon to afford perfluoroalkylated β-amino acids in good yield.The reaction of fluoroalky
