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• W2951244037 abstract "Organocatalytic asymmetric reactions have proved to be efficient and powerful tools in organic synthesis. Among them, the asymmetric Michael reaction of nitroolefins with carbon nucleophiles is widely recognized as one of the most important and versatile processes for the synthesis of enantioselective C-C and C-X bonds; for the nitroolefins are of special interest as excellent Michael acceptors, and the nitro functionality can be easily transformed into an amine, nitrile oxide, ketone, carboxylic acid, hydrogen, etc., providing a wide range of synthetically interesting compounds. Because of the growing need for environment-friendly asymmetric synthesis, considerable attention has been focused on the development of efficient small-molecule chiral organocatalysts for asymmetric reactions; among which, the catalysts typically used for the asymmetric Michael reaction of nitroolefins are proline and its analoguederived secondary amines. By now, chiral pyrrolidine-urea(thiourea)-based organocatalysts have been widely used in asymmetric catalysis due to that the bifunctional thiourea catalysts could activate both nitroolefins and nucleophiles simultaneously and control the approach of nucleophiles to nitroolefins. Meanwhile, ionic liquids have been widely used as environmentally benign solvents to replace common organic media. Moreover, they are reusable, allow for simple isolation of products and enable the easy recovery of catalysts. More interesting is the enhancement of reaction efficiency by using ionic liquids as solvents. Herein we wish to report a novel ionic liquid-solutable pyrrolidine-thiourea that promotes the asymmetric Michael reaction of nitroolefins in ionic liquid; this reaction system will make the process more environmentally benign and more economical. The novel catalyst was synthesized from the “chiral pool” using L-Proline as a starting material (Scheme 1). The synthetic procedures were quite straightforward and afforded the product in 15% total yield from L-proline (9 steps). The catalyst obtained is soluble in ionic liquids and water, but insoluble in many organic solvents. These properties, together with the straightforward synthesis, suffice for practical applications in asymmetric synthesis. We first choose the addition of cyclohexanone to (2nitrovinyl)-benzene as our research model to evaluate the novel chiral catalysts, and optimize the reaction conditions. A serise of ionic liquid solvents are first examined for the" @default.
• W2951244037 created "2019-06-27" @default.
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• W2951244037 date "2013-11-20" @default.
• W2951244037 modified "2023-10-07" @default.
• W2951244037 title "Asymmetric Michael Addition of Ketones to Nitroolefins Catalyzed by a Novel Chiral Pyrrolidine-Thiourea in the Ionic Liquid" @default.
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• W2951244037 doi "https://doi.org/10.5012/bkcs.2013.34.11.3179" @default.
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