Combined bead polymerization and Cinchona organocatalyst immobilization by thiol–ene addition
作者： Kim A Fredriksen , Tor E Kristensen , Tore Hansen
DOI: 10.3762/BJOC.8.125
关键词: Chemistry 、 Organic chemistry 、 Organocatalysis 、 Alkene 、 Ene reaction 、 Thiol-ene reaction 、 Polymer chemistry 、 Cinchona 、 Polymer 、 Polymerization 、 Enantioselective synthesis
摘要: In this work, we report an unusually concise immobilization of Cinchona organocatalysts using thiol–ene chemistry, in which catalyst and bead polymerization is combined a single step. A solution azo initiator, polyfunctional thiol, alkene unmodified Cinchona-derived organocatalyst solvent suspended water copolymerized on heating by additions. The resultant spherical gel-type polymer beads have been evaluated as catalytic asymmetric transformations.
sci-hub.se 参考文章(20)
Tor Erik Kristensen, Tore Hansen, Synthesis of Chiral Catalysts Supported on Organic Polymers Catalytic Methods in Asymmetric Synthesis: Advanced Materials, Techniques, and Applications. pp. 209- 256 ,(2011) , 10.1002/9781118087992.CH4
Jiale Song, Lixin Chen, Yazhou Wang, Weiwei Chen, Rumin Wang, Kinetics of UV curable alkyl 3-mercaptopropionate-vinyl silizane Frontiers of Chemical Engineering in China. ,vol. 2, pp. 390- 395 ,(2008) , 10.1007/S11705-008-0080-6
Michelangelo Gruttadauria, Francesco Giacalone, Renato Noto, Water in Stereoselective Organocatalytic Reactions Advanced Synthesis & Catalysis. ,vol. 351, pp. 33- 57 ,(2009) , 10.1002/ADSC.200800731
Maria Kempe, George Barany, CLEAR : A NOVEL FAMILY OF HIGHLY CROSS-LINKED POLYMERIC SUPPORTS FOR SOLID-PHASE PEPTIDE SYNTHESIS Journal of the American Chemical Society. ,vol. 118, pp. 7083- 7093 ,(1996) , 10.1021/JA954196S
Philip Hedge, Ezzatollah Khoshdel, Janette Waterhouse, Jean M. J. Fréchet, Michael additions catalysed by cinchona alkaloids bound via their vinyl groups to preformed crosslinked polymers Journal of The Chemical Society-perkin Transactions 1. ,vol. 17, pp. 2327- 2331 ,(1985) , 10.1039/P19850002327
Ying-Chun Chen, Bang-Jing Li, Lin Jiang, Min Liu, Li-Sheng Ding, Yong Wu, Asymmetric Michael Addition of Arylthiols to α,β-Unsaturated Carbonyl Compounds Catalyzed by Bifunctional Organocatalysts Synlett. ,vol. 2005, pp. 603- 606 ,(2005) , 10.1055/S-2005-863710
Xacobe C Cambeiro, Rafael Martín-Rapún, Pedro O Miranda, Sonia Sayalero, Esther Alza, Patricia Llanes, Miquel A Pericàs, Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline. Beilstein Journal of Organic Chemistry. ,vol. 7, pp. 1486- 1493 ,(2011) , 10.3762/BJOC.7.172
Henk Hiemstra, Hans Wynberg, ADDITION OF AROMATIC THIOLS TO CONJUGATED CYCLOALKENONES, CATALYZED BY CHIRAL BETA-HYDROXY AMINES - A MECHANISTIC STUDY ON HOMOGENEOUS CATALYTIC ASYMMETRIC-SYNTHESIS Journal of the American Chemical Society. ,vol. 103, pp. 417- 430 ,(1981) , 10.1021/JA00392A029
Theodor Posner, Beiträge zur Kenntniss der ungesättigten Verbindungen. II. Ueber die Addition von Mercaptanen an ungesättigte Kohlenwasserstoffe European Journal of Inorganic Chemistry. ,vol. 38, pp. 646- 657 ,(1905) , 10.1002/CBER.190503801106
Tor E. Kristensen, Kristian Vestli, Martin G. Jakobsen, Finn K. Hansen, Tore Hansen, A general approach for preparation of polymer-supported chiral organocatalysts via acrylic copolymerization. Journal of Organic Chemistry. ,vol. 75, pp. 1620- 1629 ,(2010) , 10.1021/JO902585J