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N. Mase, Y. Nakai, Naoko Ohara, H. Yoda, K. Takabe, F. Tanaka, C. Barbas (2006)
Organocatalytic direct asymmetric aldol reactions in water.Journal of the American Chemical Society, 128 3
Jian-Fei Bai, Yunlong Guo, Lin Peng, Li-Na Jia, Xiao‐Ying Xu, Li‐Xin Wang (2013)
Enantioselective Diels–Alder reaction of anthrone and maleimide catalyzed by a simple chiral tertiary amineTetrahedron, 69
P. Watts, C. Wiles (2007)
Recent advances in synthetic micro reaction technology.Chemical communications, 5
C. Wiles, P. Watts (2014)
Continuous process technology: a tool for sustainable productionGreen Chemistry, 16
D. Font, S. Sayalero, Amaia Bastero, C. Jimeno, M. Pericàs (2008)
Toward an artificial aldolase.Organic letters, 10 2
K. Elvira, Xavier Solvas, R. Wootton, A. deMello (2013)
The past, present and potential for microfluidic reactor technology in chemical synthesis.Nature chemistry, 5 11
Y Nakai N Mase (2005)
10.1021/ja0573312J. Am. Chem. Soc., 128
T. Tsubogo, T. Ishiwata, S. Kobayashi (2013)
Asymmetric carbon-carbon bond formation under continuous-flow conditions with chiral heterogeneous catalysts.Angewandte Chemie, 52 26
C. Ayats, A. Henseler, M. Pericàs (2012)
A solid-supported organocatalyst for continuous-flow enantioselective aldol reactions.ChemSusChem, 5 2
Rajesh Munirathinam, J. Huskens, W. Verboom (2014)
Piperazine-Containing Polymer Brush Layer as Supported Base Catalyst in a Glass MicroreactorJournal of Flow Chemistry, 4
Hala Eldaroti, S. Gadir, M. Refat, A. Adam (2013)
Charge-transfer interaction of drug quinidine with quinol, picric acid and DDQ: Spectroscopic characterization and biological activity studies towards understanding the drug–receptor mechanismJournal of Pharmaceutical Analysis, 4
Y. Arakawa, H. Wennemers (2013)
Enamine catalysis in flow with an immobilized peptidic catalyst.ChemSusChem, 6 2
Chun-Kit Hau, Hao He, A. Lee, D. Chik, Zongwei Cai, H. Wong (2010)
Enantioselective Brønsted base catalyzed [4+2] cycloaddition using novel amino-substituted tetraphenylene derivativesTetrahedron, 66
F. Costantini, E. Benetti, D. Reinhoudt, J. Huskens, G. Vancso, W. Verboom (2010)
Enzyme-functionalized polymer brush films on the inner wall of silicon-glass microreactors with tunable biocatalytic activity.Lab on a chip, 10 24
E. Alza, Carles Rodríguez-Escrich, S. Sayalero, Amaia Bastero, M. Pericàs (2009)
A solid-supported organocatalyst for highly stereoselective, batch, and continuous-flow Mannich reactions.Chemistry, 15 39
T Mayer-Gall J-W Lee (2013)
10.1126/science.1242196Science, 341
Rajesh Munirathinam, D. Joe, J. Huskens, W. Verboom (2012)
Regioselectivity Control of the Ring Opening of Epoxides With Sodium Azide in a MicroreactorJournal of Flow Chemistry, 2
Sándor Otvös, I. Mándity, F. Fülöp (2012)
Highly efficient 1,4-addition of aldehydes to nitroolefins: organocatalysis in continuous flow by solid-supported peptidic catalysts.ChemSusChem, 5 2
B. List (2002)
Proline-catalyzed asymmetric reactionsTetrahedron, 58
P Watts (2007)
Chem. Commun.
Rajesh Munirathinam, R. Ricciardi, R. Egberink, J. Huskens, Michael Holtkamp, H. Wormeester, U. Karst, W. Verboom (2013)
Gallium-containing polymer brush film as efficient supported Lewis acid catalyst in a glass microreactorBeilstein Journal of Organic Chemistry, 9
F. Costantini, W. Bula, R. Salvio, J. Huskens, H. Gardeniers, D. Reinhoudt, W. Verboom (2009)
Nanostructure based on polymer brushes for efficient heterogeneous catalysis in microreactors.Journal of the American Chemical Society, 131 5
F. Costantini, E. Benetti, R. Tiggelaar, H. Gardeniers, D. Reinhoudt, J. Huskens, G. Vancso, W. Verboom (2010)
A brush-gel/metal-nanoparticle hybrid film as an efficient supported catalyst in glass microreactors.Chemistry, 16 41
I. Catalytic Asymmetric Synthesis Ojima (2010)
Hoboken
Xiaoying Liu, Barış Ünal, K. Jensen (2012)
Heterogeneous catalysis with continuous flow microreactorsCatalysis Science & Technology, 2
L. Osorio-Planes, Carles Rodríguez-Escrich, M. Pericàs (2012)
Polystyrene-supported (2S)-(-)-3-exo-piperazinoisoborneol: an efficient catalyst for the batch and continuous flow production of enantiopure alcohols.Organic letters, 14 7
Wei Wang, Xuebing Ma, Jingwei Wan, Junhong Cao, Qian Tang (2012)
Preparation and confinement effect of a heterogeneous 9-amino-9-deoxy-epi-cinchonidine organocatalyst for asymmetric aldol addition in aqueous medium.Dalton transactions, 41 18
A Leoncini (2013)
Supported chiral proline and pyrrolidine organocatalysts for enantioselective C-C bond formation reactions
In case of the Diels-Alder reaction, a direct comparison of the wallcoated versus the packed-bed approach results was not possible due to lack of relevant literature data.
case of the Diels-Alder reaction
A. Massi, A. Cavazzini, L. Zoppo, O. Pandoli, Valentina Costa, L. Pasti, P. Giovannini (2011)
Toward the optimization of continuous-flow aldol and α-amination reactions by means of proline-functionalized silicon packed-bed microreactorsTetrahedron Letters, 52
A. Karim, J. Bravo, David Gorm, Travis Conant, A. Datye (2005)
Comparison of wall-coated and packed-bed reactors for steam reforming of methanolCatalysis Today, 110
A. Bogdan, B. Mason, Kevin Sylvester, D. McQuade (2007)
Improving solid-supported catalyst productivity by using simplified packed-bed microreactors.Angewandte Chemie, 46 10
M. Brivio, W. Verboom, D. Reinhoudt (2006)
Miniaturized continuous flow reaction vessels: influence on chemical reactions.Lab on a chip, 6 3
D. Bergbreiter (2010)
Catalytic Asymmetric Synthesis, 3rd ed Catalytic Asymmetric Synthesis, 3rd ed . Edited by Iwao Ojima (Stony Brook University, Stony Brook, NY). John Wiley & Sons, Inc.: Hoboken, NJ. 2010. xviii + 998 pp. $175.00. ISBN 978-0-470-17577-4 .Journal of the American Chemical Society, 132
O. Riant, H. Kagan (1990)
Asymmetric Diels-Alder reaction catalyzed by chiral basesTetrahedron Letters, 30
Dongbo Zhao, K. Ding (2013)
Recent Advances in Asymmetric Catalysis in FlowACS Catalysis, 3
Ravindra Jumde, A. Mandoli, F. Lorenzi, D. Pini, P. Salvadori (2010)
Simple Preparation of Dimeric Cinchona Alkaloid Derivatives on Polystyrene Supports and a Highly Enantioselective Catalytic Heterogeneous Dimerization of KetenesAdvanced Synthesis & Catalysis, 352
R. Ricciardi, Rajesh Munirathinam, J. Huskens, W. Verboom (2014)
Improved catalytic activity and stability using mixed sulfonic acid- and hydroxy-bearing polymer brushes in microreactors.ACS applied materials & interfaces, 6 12
Muhammad Irfan, T. Glasnov, C. Kappe (2011)
Heterogeneous catalytic hydrogenation reactions in continuous-flow reactors.ChemSusChem, 4 3
M. Pericàs, C. Herrerías, L. Solà (2008)
Fast and Enantioselective Production of 1‐Aryl‐1‐propanols through a Single Pass, Continuous Flow ProcessAdvanced Synthesis & Catalysis, 350
K. Kacprzak, N. Maier, W. Lindner (2006)
Highly efficient immobilization of Cinchona alkaloid derivatives to silica gel via click chemistryTetrahedron Letters, 47
B. Gisin (1972)
The monitoring of reactions in solid-phase peptide synthesis with picric acid.Analytica chimica acta, 58 1
Ryan Hartman, J. McMullen, K. Jensen (2011)
Deciding whether to go with the flow: evaluating the merits of flow reactors for synthesis.Angewandte Chemie, 50 33
E. Klemm, H. Doring, A. Geißelmann, S. Schirrmeister (2007)
Microstructured Reactors in Heterogenous CatalysisChemical Engineering & Technology, 30
Abstract Cinchona alkaloid and proline derivatives as enantioselective catalysts were covalently attached onto the inner walls of a microreactor using glycidyl methacrylate polymer brushes. The successful formation of the organocatalystfunctionalized brush layers on flat silicon oxide surfaces was confirmed by several techniques such as Fourier transform infrared (FT-IR), ellipsometry, and X-ray photoelectron spectroscopy (XPS). The applicability of the cinchona alkaloid (cinchonidine or quinidine)- and proline-containing polymer brushes in a microreactor was demonstrated for the Diels-Alder reaction between anthrone and N-substituted maleimides, and the aldol reaction between 4-nitrobenzaldehyde and cyclohexanone, respectively, which showed moderate conversions (up to 55% and 23%, respectively) and moderate to good enantioselectivities (up to 55% and 93%, respectively). The pristine catalytic activity of the microreactor was intact even after 1 month.
Journal of Flow Chemistry – Springer Journals
Published: Jan 1, 2015
Keywords: chemistry/food science, general; green chemistry; organic chemistry; inorganic chemistry; nanochemistry; industrial chemistry/chemical engineering
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