98184-92-0Relevant academic research and scientific papers
Features of two- and multicomponent heterocyclization reactions involving 3,4-disubstituted 5-aminopyrazoles and alkyl pyruvates
Sakhno, Yana I.,Kozyryev, Anton V.,Desenko, Sergey M.,Shishkina, Svetlana V.,Musatov, Vladimir I.,Sysoiev, Dmytro O.,Chebanov, Valentin A.
, p. 564 - 571 (2018)
Three-component heterocyclizations of pyruvic acids and their esters with 5-aminopyrazoles and aromatic aldehydes, in addition to the sequential versions of these reactions, under different activating conditions were studied. Under conventional heating, p
Stereoselective Organocatalytic Construction of Spiro Oxindole Pyrrolidines Using Unsaturated α-Ketoesters and α-Ketoamides
Peňa?ka, Tibor,Palchykov, Vitalii,Rakovsky, Erik,Addová, Gabriela,?ebesta, Radovan
supporting information, p. 1693 - 1703 (2021/03/15)
We have investigated the stereoselective formation of spiro oxindole pyrrolidines via formal [3+2] cycloaddition of oxindole imines with ketoesters and ketoamides. Bifunctional squaramide organocatalyst was able to induce enantioselectivity of up to 60 %
Asymmetric 1,4-Addition of Arylboronic Acids to β,γ-Unsaturated α-Ketoesters using Heterogeneous Chiral Metal Nanoparticle Systems
Miyamura, Hiroyuki,Yasukawa, Tomohiro,Zhu, Zhiyuan,Kobayashi, Shū
supporting information, p. 353 - 359 (2019/12/15)
Asymmetric 1,4-addition reactions with β,γ-unsaturated α-ketoesters are valuable because the resulting chiral ketoester compounds can be converted into various useful species that are often used as chiral building blocks in drug and natural product synthesis. However, β,γ-unsaturated α-ketoesters have two reactive points in terms of nucleophilic additions, which will lead to the 1,4-adduct, the 1,2-adduct and to the combined 1,4- and 1,2-adduct. Therefore, controlling this chemoselectivity is an important factor for the development of these transformations. Here, we developed an asymmetric 1,4-addition of aryl boronic acids to β,γ-unsaturated α-ketoesters by using heterogeneous chiral rhodium nanoparticle systems with a chiral diene ligand bearing a secondary amide moiety. The newly developed polydimethylsilane-immobilized rhodium nanoparticle catalysts showed high activity, high chemoselectivity, and excellent enantioselectivity, and this is the first heterogeneous catalytic system for this asymmetric reaction. Metal nanoparticle catalysts were recovered and reused without loss of activity or leaching of metal. (Figure presented.).
Iodine mediated a simple strategy for the synthesis of β,γ-unsaturated-α-ketoesters and its application for the synthesis of 4,5-dihydropyrazole derivatives
Pommidi, Anil,Shaik, Asha Begum,Chatterjee, Anindita,Somarapu, Vijaya Laxmi
, p. 1545 - 1553 (2020/03/05)
Abstract: Novel and efficient method for the synthesis of a series of β,γ-unsaturated-α-ketoesters under mild conditions was developed. This one-step protocol was achieved by the reaction of electron-rich aromatic aldehydes and pyruvates in the presence o
Diversity-Oriented Synthesis of Spirocyclohexene Indane-1,3-diones and Coumarin-Fused Cyclopentanes via an Organobase-Controlled Cascade Reaction
Wang, Min,Tseng, Ping-Yao,Chi, Woei-Jye,Suresh, Sundaram,Edukondalu, Athukuri,Chen, Yi-Ru,Lin, Wenwei
supporting information, p. 3407 - 3415 (2020/07/16)
An organobase-controlled, divergent cascade reaction to construct spirocyclohexene indane-1,3-diones and coumarin-fused cyclopentanes is reported. The cascade reaction is triggered by the 1,6-addition of 3-homoacylcoumarins to the indanedione-derived acce
Direct Synthesis of β,γ-Unsaturated α-Keto Esters from Aldehydes and Pyruvates
Mansaray, John Kamanda,Sun, Jiarui,Huang, Shisheng,Yao, Weijun
supporting information, p. 809 - 813 (2019/04/25)
Herein, we describe two practical methods to synthesize β,γ-unsaturated α-keto esters directly from aldehydes and pyruvates promoted by BF 3 ?Et 2 O in the presence of Ac 2 O or by Ti(OEt) 4 under mild condition
Synthesis of 1,2-Dicarbonyl-3-enes by Hydroacylation of 1-Alkynes with Glyoxal Derivatives Using Metal-Organic Framework Cu/MOF-74 as Heterogeneous Catalyst
Nguyen, Nguyen B.,Dang, Giao H.,Le, Dung T.,Truong, Thanh,Phan, Nam T. S.
, p. 361 - 369 (2016/04/26)
A crystalline copper-based metal-organic framework Cu/MOF-74 was synthesized, and used as an efficient heterogeneous catalyst for the synthesis of 1,2-dicarbonyl-3-enes by means of the hydroacylation of 1-alkynes with glyoxal derivatives in the presence o
CuBr-promoted formal hydroacylation of 1-alkynes with glyoxal derivatives: An unexpected synthesis of 1,2-dicarbonyl-3-enes
Chen, Shufeng,Li, Xiaojie,Zhao, Haiying,Li, Baoguo
, p. 4137 - 4141 (2014/05/20)
An efficient and concise protocol has been developed for the highly regio- and stereoselective synthesis of E-1,2-dicarbonyl-3-ene derivatives by a copper-promoted reaction of 1-alkynes with α-carbonyl aldehydes in the presence of morpholine. The products obtained are believed as the formal hydroacylation of the triple bond.
Synthesis in ionic liquids only: Access to α-oxo-γ-thio-esters via Mukaiyama coupling
Jebri, Khouloud,Mazières, Marie-Rose,Ballereau, Stéphanie,Ben Ayed, Ta?cir,Plaquevent, Jean-Christophe,Baltas, Michel,Guillen, Frédéric
, p. 1353 - 1356 (2014/03/21)
Ionic liquids are solvents general enough to conduct a multi-step process in organic synthesis. We show that both the preparation of starting materials (thioacetals and enoxysilane) as well as their coupling can be realized in such medium.
A mild method for indium(III)-catalyzed 1,4-hydrosilylation of α,β-enone esters with triethylsilane and trifluoroacetic acid
Xing, Ping,Zang, Wei,Huang, Zuo-Gang,Zhan, Yue-Xiong,Zhu, Chuan-Jun,Jiang, Biao
, p. 2269 - 2273 (2012/10/30)
A chemo- and stereoselective 1,4-hydrosilylation of α,β-enone esters was developed using triethylsilane and trifluoroacetic acid under indium chloride catalysis. Georg Thieme Verlag Stuttgart ? New York.
