141377-55-1Relevant articles and documents
Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine
Trost, Barry M.,Yeh, Vince S. C.,Ito, Hisanako,Bremeyer, Nadine
, p. 2621 - 2623 (2002)
(Matrix presented) Syntheses of variously modified ligands for the dinuclear zinc catalysts for the asymmetric aldol and nitroaldol (Henry) reactions are reported. Catalytic enantioselective nitroaldol reactions promoted by these modified ligands led to efficient syntheses of the β-preceptor agonists (-)-denopamine and (-)-arbutamine.
Synthesis of hindered chiral guanidine bases starting from (S)-(N,N-dialkyl-aminomethyl)pyrrolidines and BrCN
Koehn, Uwe,Klopfleisch, Maurice,Goerls, Helmar,Anders, Ernst
, p. 811 - 818 (2006)
An efficient method for the preparation of hindered chiral guanidines using cyanogen bromide is described. The reaction between BrCN and vicinal diamines derived from (S)-2-(N,N-dialkyl-aminomethyl)-pyrrolidines provides chiral substituted cyanamides. The cyanamide derivatives reacted with secondary amines in hexafluoroisopropanol at reflux to form chiral hindered guanidines, which were isolated in good to excellent yields (70-96%). The chiral guanidines were prepared in an effort to design sophisticated chiral guanidine catalysts for asymmetric synthesis.
Levopimaric acid derived 1,2-diamines and their application in the copper-catalyzed asymmetric Henry reaction
Khlebnikova, Tatiana B.,Konev, Vasily N.,Pai, Zinaida P.
, p. 260 - 267 (2018)
Levopimaric acid, a readily available starting material, was used in efficient syntheses of new enantiopure diamines and Schiff bases with good yields. The synthetic procedure is based on the fumaropimaric acid monomethyl ester conversion into the optical
Enantioselective Henry reaction catalyzed by trianglamine-Cu(OAc)2 complex under solvent-free conditions
Tanaka, Koichi,Hachiken, Satoshi
, p. 2533 - 2536 (2008)
Chiral trianglamine-Cu(OAc)2 complex was found to be an efficient catalyst for enantioselective Henry reaction between nitromethane and various aldehydes to provide β-hydroxynitoroalkanes with high enantiomeric excesses under solvent-free condi
Unprecedented Mechanism of an Organocatalytic Route to Conjugated Enynes with a Junction to Cyclic Nitronates
Streitferdt, Verena,Haindl, Michael H.,Hioe, Johnny,Morana, Fabio,Renzi, Polyssena,von Rekowski, Felicitas,Zimmermann, Alexander,Nardi, Martina,Zeitler, Kirsten,Gschwind, Ruth M.
supporting information, p. 328 - 337 (2018/11/23)
Conjugated enynes as well as cyclic nitronates are crucial building blocks for numerous natural products and pharmaceuticals. However, so far, no common and metal-free synthetic route to both conjugated enynes and cyclic nitronates has been reported. Herein, in situ NMR, labelling studies and theoretical calculations were combined to investigate the mechanism of the unusual triple bond formation towards conjugated enynes. Starting from nitroalkene dimers, first an isoxazolidine-2,5-diol derivative is formed as central intermediate. From this, enynes were generated by a combination of oxidation, dehydration, and retro 1,3-dipolar cycloaddition, whereas for nitronates a base induced intramolecular reorganization is proposed. While the product distribution could be controlled and high yields of nitronate were achieved, only medium to good yields for enynes were obtained due to polymerization losses. Nevertheless, we hope that these mechanistic investigations may provide a basis for further developments of organocatalytic or metal-free preparations of conjugated enynes and nitronates.
Synthesis of unsaturated silyl nitronates via the silylation of conjugated nitroalkenes
Khotyantseva, Elizaveta A.,Tabolin, Andrey A.,Novikov, Roman A.,Nelyubina, Yulia V.,Ioffe, Sema L.
supporting information, p. 3128 - 3131 (2018/07/13)
A new method for the synthesis of conjugated silyl nitronates from nitroalkenes is described. The procedure has wide substrate scope and is compatible with in situ generation of the substrates from 2-nitroalcohols or 2-chloro-nitroalkanes. A cascade transformation to give 3,4,5,6-tetrahydropyridine N-oxide derivatives was disclosed.
