82794-36-3Relevant academic research and scientific papers
Multicomponent, Enantioselective Michael-Michael-Aldol-β-Lactonizations Delivering Complex β-Lactones
Van, Khoi N.,Romo, Daniel
, p. 632 - 643 (2018/01/27)
Optically active, tertiary amine Lewis bases react with unsaturated acid chlorides to deliver chiral, α,β-unsaturated acylammonium salts. These intermediates participate in a catalytic, enantioselective, three-component process delivering bi- and tricyclic β-lactones through a Michael-Michael-aldol-β-lactonization. In a single operation, the described multicomponent, organocascade process forms complex bi- and tricyclic β-lactones by generating four new bonds, two rings, and up to four contiguous stereocenters. In the racemic series, yields of 22-75% were achieved using 4-pyrrolidinopyridine as Lewis base. In the enantioselective series employing isothiourea catalysts, a kinetic resolution of the initially formed racemic Michael adduct appears operative, providing yields of 46% to quantitative (based on 50% max) with up to 94:6 er. Some evidence for a dynamic kinetic asymmetric transformation for tricyclic-β-lactone 1d was obtained following optimization (yields up to 61%, 94:6 er) through a presumed reversible Michael.
Copper-Catalyzed Dehydrogenative Diels-Alder Reaction
Jiang, Bing,Liang, Qiu-Ju,Han, Yu,Zhao, Meng,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 3215 - 3219 (2018/06/11)
A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.
2 - methyl malonic acid diester synthetic method of the compound
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Paragraph 0054-0056, (2017/08/10)
The invention discloses a synthetic method of 2-diester methylmalonate compounds, and relates to the technical field of carboxylic ester preparation. The synthetic method comprises steps as follows: C, sulfonic acid 2-ethyl N-cyanoethanimideate IV and cyanide react under the action of a solvent and a catalyst, and 2-methyl malononitrile V is obtained; D, 2-methyl malononitrile V and ROH react under the action of the solvent and concentrated sulfuric acid, and products of 2-diester methylmalonate compounds I are obtained, wherein MCN is cyanide, M is Na or K, ROH is alkyl alcohol, alkenyl alcohol or a fluoride group containing alcohol, is benzyl alcohol or benzyl alkyl, halogen or nitro substituted benzyl alcohol, or is phenol or C1-C5 containing alkyl, halogen or nitro substituted phenol. The method is unique, the reaction conditions are mild, the reaction process is basically free of by-products, the yield is high, adopted raw materials have extensive sources, and acetaldehyde can be used as the raw material; the synthetic method is applicable to industrial production.
Introduction of the 4,4,4-Trifluorobut-2-ene Chain Exploiting a Regioselective Tsuji-Trost Reaction Catalyzed by Palladium Nanoparticles
Hemelaere, Rémy,Desroches, Justine,Paquin, Jean-Fran?ois
supporting information, p. 1770 - 1773 (2015/04/14)
A palladium-nanoparticle-catalyzed Tsuji-Trost reaction of 4,4,4-trifluorobut-2-en-1-yl acetate and ethyl(4,4,4-trifluorobut-2-en-1-yl)carbonate was accomplished with various nucleophiles including phenols, amines, and malonates. In the case of the phenols, isomerization of the double bond in the product (up to 20%) was observed as a side reaction. Further synthetic transformations including hydrogenation, the Diels-Alder reaction, and asymmetric dihydroxylation of a product were also examined.
Air- and water-tolerant rare earth guanidinium BINOLate complexes as practical precatalysts in multifunctional asymmetric catalysis
Robinson, Jerome R.,Fan, Xinyuan,Yadav, Jagjit,Carroll, Patrick J.,Wooten, Alfred J.,Pericàs, Miquel A.,Schelter, Eric J.,Walsh, Patrick J.
supporting information, p. 8034 - 8041 (2014/06/23)
Shibasaki's REMB catalysts (REMB; RE = Sc, Y, La-Lu; M = Li, Na, K; B = 1,1′-bi-2-naphtholate; RE/M/B = 1/3/3) are among the most enantioselective asymmetric catalysts across a broad range of mechanistically diverse reactions. However, their widespread us
Direct catalytic asymmetric synthesis of N-heterocycles from commodity acid chlorides by employing α,β-unsaturated acylammonium salts
Vellalath, Sreekumar,Van, Khoi N.,Romo, Daniel
supporting information, p. 13688 - 13693 (2014/01/06)
Taming the beast, asymmetrically: Modulation of the reactivity of acid chlorides, using cinchona alkaloid catalysts, results in chiral α,β-unsaturated acylammoniums, which react with nucleophiles enantioselectively to give pyrrolidinones, piperid-2-ones,
Copper(II) triflate catalyzed amination and aziridination of 2-Alkyl substituted 1,3-dicarbonyl compounds
Ton, Thi My Uyen,Tejo, Ciputra,Tiong, Diane Ling Ying,Chan, Philip Wai Hong
experimental part, p. 7344 - 7350 (2012/06/16)
A method to prepare α-acyl-β-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)2 + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI=NTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic C-H bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the β-aminated adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2-3 equiv was discovered to result in preferential formal aziridination of the C-C bond of the 2-alkyl substituent of the starting material and formation of the aziridine product.
Sml2-mediated carbon-carbon bond fragmentation in a-aminomethyl malonates
Xu, Qiongfeng,Cheng, Bin,Ye, Xinshan,Zhai, Hongbin
supporting information; experimental part, p. 4136 - 4138 (2009/12/30)
A new and efficient samarium diiodide-promoted carbon-carbon bond fragmentation reaction of α-aminomethyl malonates, taking place normally at room temperature and generating the corresponding deaminomethylation products In 74-94% yields, is reported. The presence of the amino group Is necessary for the success of the current transformation.
Inhibition of aminopeptidases by peptides containing ketomethylene and hydroxyethylene amide bond replacements
Harbeson,Rich
, p. 1378 - 1392 (2007/10/02)
Inhibitors of aminopeptidase enzymes have been prepared by the synthesis of peptide substrate analogues in which the scissile amide bond has been replaced with the hydrolytically stable ketomethylene (-COCH2-) and hydroxyethylene [-CH(OH)CHsub
Carbon-carbon bond formation under aqueous reaction conditions using sulfonium and selenonium salt electrophiles
Winkler,Finck-Estes
, p. 7293 - 7296 (2007/10/02)
Methylation of relatively acidic (pK(a) 13) carbon nucleophiles occurs at neutral pH in aqueous media using suitably substituted methyl sulfonium and selenonium salt electrophiles.
