439077-75-5Relevant academic research and scientific papers
Highly enantioselective aza-Baylis-Hillman reaction in a chiral reaction medium
Gausepohl, Rolf,Buskens, Pascal,Kleinen, Jochen,Bruckmann, Angelika,Lehmann, Christian W.,Klankermayer, Juergen,Leitner, Walter
, p. 3689 - 3692 (2006)
Let's twist again! The first highly enantioselective asymmetric reaction in which a chiral reaction medium is the sole source of chirality is presented. The aza-Baylis-Hillman reaction in an ionic liquid with a chiral anion, whose design is based on mecha
Highly flexible fibre-optic ATR-IR probe for inline reaction monitoring
Minnich, Clemens B.,Buskens, Pascal,Steffens, H. Christian,Baeuerlein, Patrick S.,Butvina, Leonid N.,Kuepper, Lukas,Leitner, Walter,Liauw, Marcel A.,Greiner, Lasse
, p. 94 - 97 (2007)
Near infrared (IR) applications have considerably profited from the use of flexible and robust fibre-optical probes. So far, a comparable technique for mid-IR was not available due to low stability and lack of robustness of the fibres. We report the use of a newly developed miniaturised diamond ATR-probe with high chemical resistance and pressure resistance based on robust fibre optics. The routine and convenient application in a glove box to highly air- and oxygen-sensitive reactions on a millilitre scale is reported, as well as the monitoring of a solventless reaction on a litre scale.
Bifunctional activation and racemization in the catalytic asymmetric Aza-Baylis-Hillman reaction
Buskens, Pascal,Klankermayer, Juergen,Leitner, Walter
, p. 16762 - 16763 (2005)
The mechanism of bifunctional activation in the asymmetric aza-Baylis-Hillman (aza-BH) reaction was studied using NMR spectroscopic techniques. The reaction involves rate-limiting proton transfer in the absence of added protic species, but exhibits no aut
Switchable pyrrole-based hydrogen bonding motif in enantioselective trifunctional organocatalysis
Eliseenko, Sviatoslav S.,Liu, Fei
, p. 518 - 526 (2019/01/04)
Pyrroles are versatile chemical motifs for molecular recognition or ligand design but their utility as catalytic components are underexplored. We incorporated a pyrrole motif into our acid-switchable, MAP-based trifunctional organocatalytic system. The sw
The Aza-Morita-Baylis-Hillman reaction: A mechanistic and kinetic study
Lindner, Christoph,Liu, Yinghao,Karaghiosoff, Konstantin,Maryasin, Boris,Zipse, Hendrik
supporting information, p. 6429 - 6434 (2013/07/05)
The aza-Morita-Baylis-Hillman (aza-MBH) reaction has been studied in a variety of solvents, a selection of imine substrates and with various combinations of PPh3 and para-nitrophenol as the catalyst system. The measured kinetic data indicates that the effects of solvent and protic co-catalyst are strongly interdependent. These results are most easily reconciled with a mechanistic model involving the reversible protonation of zwitterionic intermediates in the catalytic cycle, which is also supported by 31P NMR spectroscopy and quantum chemical studies. Copyright
2-(Diphenylphosphino)benzoyl-substituted calix[4]arene: Efficient organocatalyst in aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone
Shen, Yanyan,Tang, Qian,Zhang, Chenchen,Zhong, Weihui
supporting information; experimental part, p. 741 - 746 (2012/07/13)
A novel bifunctional organocatalyst 5,11,17,23-tetra-butyl-25-[2- (diphenylphosphino)benzoate]-26,27,28-trihydroxycalix-[4]arene (LB3) was synthesized and applied to promote the aza-Morita-Baylis-Hillman (aza-MBH) reaction of N-sulfonated im-ines with met
The aza-Morita-Baylis-Hillman reaction of electronically and sterically deactivated substrates
Lindner, Christoph,Tandon, Raman,Liu, Yinghao,Maryasin, Boris,Zipse, Hendrik
supporting information; experimental part, p. 3210 - 3218 (2012/06/04)
The aza-Morita-Baylis-Hillman (azaMBH) reaction has been studied for electronically and sterically deactivated Michael acceptors. It is found that electronically deactivated systems can be converted with electron-rich phosphanes and pyridines as catalysts
Aza-Morita-Baylis-Hillman reaction with ion-supported Ph3P
Imura, Yumi,Shimojuh, Naoya,Moriyama, Katsuhiko,Togo, Hideo
experimental part, p. 2319 - 2325 (2012/04/10)
Various N-tosyl arylimines reacted with methyl vinyl ketone and ethyl vinyl ketone in the presence of ion-supported Ph3P A and B to give adducts, N-(2′-methylene-3′-oxo-1′-arylbutyl)-4- methylbenzenesulfonamides and N-(2′-methylene-3′-oxo-1′- a
First application of air-stable and reusable phosphine-containing calix[4]arene in catalytic aza-morita-baylis-hillman reaction
Zhong, Weihui,Zheng, Yemin,Zhou, Jiadi,Shen, Yanyan
supporting information; experimental part, p. 3057 - 3060 (2011/02/22)
For the first time, the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone was catalyzed by 5,11,17,23-tetrabutyl-25- (diphenylphosphinomethoxy)-26,27,28-trihydroxycalix[4]arene (LB1), an air-stable, easily isolated and reu
Enantioselective trifunctional organocatalysts for rate-enhanced aza-Morita-Baylis-Hillman reactions at room temperature
Garnier, Jean-Marc,Anstiss, Christopher,Liu, Fei
experimental part, p. 331 - 338 (2009/11/30)
A Bronsted acid-activated trifunctional organocatalyst, based on the BINAP scaffold, was used for the first time to catalyze aza-Morita-Baylis- Hillman reactions between N-tosylimines and methyl vinyl ketone with fast reaction rates and good enantioselect
