Trifluoroethanol as a Unique Additive for the Chemoselective Electrooxidation of Enamines to Access Unsymmetrically Substituted NH-Pyrroles
An electrochemical method for the synthesis of unsymmetrically substituted NH-pyrroles is described. The synthetic strategy comprises a challenging heterocoupling between two structurally diverse enamines via sequential chemoselective oxidation, addition,
Baidya, Mrinmay,De Sarkar, Suman,Maiti, Debabrata,Roy, Lisa
(2021/12/23)
Copper-Catalyzed Tandem Reaction of Enamino Esters with ortho-Halogenated Aromatic Carbonyls: One-Pot Approach to Functionalized Quinolines
An efficient and practical approach for the synthesis of functionalized quinolines has been developed by using the copper-catalyzed tandem C–C bond formation and C–N coupling reaction of enamino esters and ortho-halogenated aromatic carbonyl compounds. Various functional groups were tolerated under the reaction conditions, and a series of quinolines were easily obtained in moderate to good yields. A gram-scale reaction was also performed to demonstrate a further application of this synthetic method.
Peng, Fei,Liu, Jin,Li, Lili,Chen, Zhiwei
supporting information
p. 666 - 672
(2018/02/14)
Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane
Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.
Ye, Jianheng,Wang, Chao,Chen, Lin,Wu, Xinjun,Zhou, Li,Sun, Jian
supporting information
p. 1042 - 1047
(2016/04/19)
Controlling the rates of reductively-activated elimination from the (indol-3-yl)methyl position of indolequinones
A series of substituted 3-(4-nitrophenyloxy)methylindole-4,7-diones (Q) were synthesised. The effects of substitution patterns on the indole core on rates of elimination of 4-nitrophenol as a model for drug release following fragmentation of a phenolic et
Everett, Steven A.,Naylor, Matthew A.,Barraja, Paola,Swann, Elizabeth,Patel, Kantilal B.,Stratford, Michael R. L.,Hudnott, Anna R.,Vojnovic, Borivoj,Locke, Rosalind J.,Wardman, Peter,Moody, Christopher J.
p. 843 - 860
(2007/10/03)
Reactions of tetrasulfur tetranitride antimony pentachloride complex (S4N4 SbCl5) with primary β-enaminones and β-enamino esters: Synthesis of 4-substituted 3-aroyl-and 3-ethoxycarbonyl-1,2,5-thiadiazoles
The reaction of tetrasulfur tetranitride antimony pentachloride complex (S4N4·SbCl5) with 3-amino-3-alkyl-1-aryl-2-propenones and 3-amino-1,3- diaryl-2-propenones in toluene at 100°C produced 4-substitued 3-aroyl-1,2,5- th
Bae, Su-Hak,Kim, Kyongtae,Park, Young Ja
p. 159 - 172
(2007/10/03)
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