Mechanistic studies on counter-ionic effects of camphorsulfonate-based ionic liquids on kinetics, thermodynamics and stereoselectivity of β-amino carbonyl compounds
Catalysis is important in various applications of organic chemistry and its output product control for stereoselective compounds is outrageous. Establishment of experimental facts of stereoselective compounds from catalysis and their validation using theoretical evidences is the key to understand various mechanisms of optically active compounds. A family of new ionic liquids (ILs) with various imidazolium cations and camphorsulfonate anion as environmentally benign liquid salts have been synthesized and deployed for catalysis of β-amino carbonyl compounds. The products were formed using ILs as a homogeneous catalyst with excellent product yield and diastereoselectivity. The effect of counter ions, Hammett acidity and viscosity of ILs along with solvent and temperature are explored in terms of reaction kinetics and product yields. Density functional theory (DFT) was used to investigate thermodynamical study of mechanistic pathway of the reaction. The DFT calculations predicted that the catalysis mechanism involved both counterions of the IL. Moreover, it is evidenced that the syn-pathway required lower activation energy while anti-pathway led to thermodynamically stable product. This study explores new avenues for using ILs as potential homogeneous catalysts for the production of stereoselective species.
Hamzah, Ahmad Sazali,Jabeen, Erum,Leveque, Jean-Marc,Sardar, Sabahat,Wilfred, Cecilia Devi
(2020/10/08)
A Convenient Regioselective Synthesis of Mannich Bases
A new, convenient regioselective process for aminomethylation of ketones is reported, involving the in situ formation of silyl enol ethers and iminium salts.
Rochin, C.,Babot, O.,Dunogues, J.,Duboudin, F.
p. 667 - 668
(2007/10/02)
N- AMINES AND AMIDES IN THE SYNTHESIS OF β-AMINO AND β-AMIDO KETONES
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Kozyukov, V. P.,Kozyukov, Vik. P.,Mironov, V. F.
p. 414 - 415
(2007/10/02)
Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. IV. The Mannich Reaction of Ketones by Means of Dihalomethane and Secondary Amine
Treatment of ketones with dihalomethane (CH2Br2, CH2ClI, and CH2I2) in the presence of secondary amine, preferably pyrrolidine, gave the corresponding Mannich base in varing yields depending on the substrate and/or combination of the reagents.
Synthese unter hohem Druck: Mannich-Reaktion von Ketonen und Estern mit Dichlormethan und sekundaeren Aminen
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Matsumoto, Kiyoshi
p. 937
(2007/10/02)
A NOVEL AMINOMETHYLATION OF SILYL ENOL ETHERS WITH AMINOMETHYL ETHERS CATALYZED BY IODOTRIMETHYLSILANE OR TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE
The iodotrimethylsilane-catalyzed reaction of silyl enol ethers with aminomethyl ethers in acetonitrile gives aminomethylation products of the corresponding ketones readily.The reaction can also be catalyzed by trimethylsilyl trifluoromethanesulfonate in dichloromethane.
Hosomi, Akira,Iijima, Susumu,Sakurai, Hideki
p. 547 - 550
(2007/10/02)
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