384354-59-0Relevant articles and documents
Effects of internal and external carboxylic acids on the reaction pathway of organocatalytic 1,4-addition reactions between aldehydes and nitroolefins
Duschmale, Joerg,Wiest, Johannes,Wiesner, Markus,Wennemers, Helma
, p. 1312 - 1318 (2013)
Kinetic and NMR spectroscopic studies revealed that the reaction pathway of conjugate addition reactions between aldehydes and nitroolefins depends on the presence or absence of a suitably positioned carboxylic acid group within the catalyst. The intermediate nitronate is trapped intramolecularly either by protonation (in the presence of a well positioned intramolecular carboxylic acid) or by C-C bond formation to a cyclobutane intermediate (in the absence of an intramolecular proton donor). These differences in the reaction pathway are reflected in different rate limiting steps of the reaction. The studies demonstrated that the preferred reaction pathway and thereby the rate limiting steps of the reaction can be influenced by additives of different acidity or the position of an intramolecular carboxylic acid group within the catalyst.
Dendrimers or nanoparticles as supports for the design of efficient and recoverable organocatalysts?
Keller, Michel,Perrier, Arnaud,Linhardt, Roland,Travers, Laurie,Wittmann, Sebastian,Caminade, Anne-Marie,Majoral, Jean-Pierre,Reiser, Oliver,Ouali, Armelle
, p. 1748 - 1754 (2013)
The Jorgensen-Hayashi catalyst [(S)-α,α-diphenylprolinol trimethylsilyl ether] was grafted onto the surface of two different supports: phosphorus dendrimers (generations 1 to 3) and magnetic, polymer-coated cobalt/carbon (Co/C) nanobeads. These new suppor
Is more better? A comparison of tri- and tetrapeptidic catalysts
Schnitzer, Tobias,Wiesner, Markus,Krattiger, Philipp,Revell, Jefferson D.,Wennemers, Helma
, p. 5877 - 5881 (2017)
From an enzymatic perspective, there is a general notion that the bigger and more complex a catalytically active peptide is the more enzyme-like and the better it should become. But is this really true? We have tackled this question firstly by screening s
Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis
De La Torre, Alexander F.,Scatena, Gabriel S.,Valdés, Oscar,Rivera, Daniel G.,Paix?o, Márcio W.
, p. 1210 - 1216 (2019)
The multicomponent synthesis of prolyl pseudo-peptide catalysts using the Ugi reaction with furfurylamines or isocyanides is described. The incorporation of such a polymerizable furan handle enabled the subsequent polymerization of the peptide catalyst wi
Environmental modulation of chiral prolinamide catalysts for stereodivergent conjugate addition
Li, Xiaowei,Zhao, Yan
, p. 126 - 133 (2022/01/27)
Synthetic chiral catalysts generally rely on proximal functional groups or ligands for chiral induction. Enzymes often employ environmental chirality to achieve stereoselectivity. Environmentally controlled catalysis has benefits such as size and shape se
Amphiphilic immobilized diphenylprolinol alkyl ether catalyst on PS-PEG resin
Koshino, Seitaro,Hattori, Shusuke,Hasegawa, Shota,Haraguchi, Naoki,Yamamoto, Takeshi,Suginome, Michinori,Uozumi, Yasuhiro,Hayashi, Yujiro
supporting information, p. 790 - 797 (2021/04/14)
Diphenylprolinol silyl ether is a widely used organocatalyst, and its immobilization on a solid support was investigated for the easy recycling and reuse of this catalyst. Because a silyl ether bond of the catalyst is weak, its alkyl ether was attached to polymers such as a polyquinoxaline-based polymer, a polystyrene polymer (PS) resin, and a polystyrenepoly(ethylene glycol) graft copolymer (PS-PEG) resin. Although a polymer-supported organocatalyst generally decreases its reactivity compared with the monomer catalyst, diphenylprolinol anthrylmethyl ether supported on PS-PEG was found to be a reactive organocatalyst; it catalyzed the Michael reaction of an aldehyde and a nitroalkene in water without an organic solvent being present, with excellent diastereo- and enantioselectivities.
N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts
?ebesta, Radovan,Górová, Renata,Kri?tofíková, Dominika,Meciarová, Mária,Némethová, Boglárka,Polácková, Viera
supporting information, p. 2629 - 2641 (2021/11/30)
The synthesis of bifunctional N-sulfinylureas and thioureas with an appended pyrrolidine unit is presented. These organocatalysts were evaluated in Michael additions of aldehydes to nitroalkenes both under solvent-free conditions and in solution. The N-su
