Communication
You have free access to this content
Synthesis and Application of Polymer-Supported Chiral Brønsted Acid Organocatalysts
Article first published online: 9 FEB 2010
DOI: 10.1002/adsc.200900746
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Rueping, M., Sugiono, E., Steck, A. and Theissmann, T. (2010), Synthesis and Application of Polymer-Supported Chiral Brønsted Acid Organocatalysts. Adv. Synth. Catal., 352: 281–287. doi: 10.1002/adsc.200900746
Publication History
- Issue published online: 17 FEB 2010
- Article first published online: 9 FEB 2010
- Manuscript Revised: 12 DEC 2009
- Manuscript Received: 29 OCT 2009
Funded by
- European Research Council. Grant Number: ERC 209437
- DFG
- RWTH Aachen University
- Evonik-Degussa
- 1For reviews on polymer-supported catalysts, see:
- 1a, , Chiral Reactions, in: Heterogeneous Catalysis, (Eds.: V. Dubois, G. Jannes), Plenum, New York, 1995, p 33;
- 1b
- 1cChiral Catalyst Immobilization and Recycling, (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, Germany, 2000;
- 1d
- 1eRecoverable Catalysts and Reagents, (Ed.: J. A. Gladysz), Chem. Rev. 2002, 102, 3215;
- 1fPolymer Supported Catalysts and Reagents in Synthetic Organic Chemistry, (Ed.: K. Janda), Bioorg. Med. Chem. Lett. 2002, 12, 1791;
- 1g
- 1h
- 1i
- 1jfor recoverable, soluble polymer-supported organic catalysts, see: , Ernst Schering Foundation Symposium Proceedings, (Eds. M. T. Reetz, B. List, S. Jaroch, H. Weinmann), Springer, Berlin, Heidelberg, 2007 p 299.
- 2For reviews on organocatalysis, see
- 2a, , Angew. Chem. 2001, 113, 3840;Angew. Chem. Int. Ed. 2001, 40, 3726;Direct Link:Direct Link:
- 2b, , Angew. Chem. 2004, 116, 5248;Angew. Chem. Int. Ed. 2004, 43, 5138;Direct Link:Direct Link:
- 2cAsymmetric Organocatalysts, (Eds.: K. N. Houk, B. List), Acc. Chem. Res. 2004, 37, 487;
- 2dAsymmetric Organocatalysis, (Eds.: A. Berkessel, H. Gröger), Wiley-VCH, Weinheim 2005;
- 2e
- 2f, , Angew. Chem. 2006, 118, 1550;Angew. Chem. Int. Ed. 2006, 45, 1520;Direct Link:Direct Link:
- 2g
- 3Examples for the immobilization of catalysts derived from Cinchona alkaloids, see:
- 3a
- 3b
- 3c
- 3d
- 3e
- 4Examples for immobilization of catalysts derived from amino acids, see:
- 4a
- 4b, , , Angew. Chem. 2000, 112, 1336;Angew. Chem. Int. Ed. 2000, 39, 1279;Direct Link:
- 4c
- 4d
- 4e
- 4f
- 4g
- 4h
- 4i, , , , , Eur. J. Org. Chem. 2004, 70, 567;
- 4j
- 4k
- 4l
- 4m
- 4n
- 4o, , , , , , Synthesis 2008, 2163;
- 4p
- 4q
- 4r
- 5Example for the immobilization of heterazolium salts: , , Adv. Synth. Catal. 2007, 349, 1851.Direct Link:
- 6Examples for the immobilization of TEMPO, see:
- 6a
- 6b
- 6c
- 7For reviews on the application of chiral BINOL derived phosphoric acids, see:
- 7a
- 7b, Angew. Chem. 2006, 118, 4013;Angew. Chem. Int. Ed. 2006, 45, 3909;Direct Link:Direct Link:
- 7c
- 7d, , , Top. Curr. Chem. 2009, DOI: 10.1007/128 2009 1.
- 8Examples for the application of chiral phosphoric acid diesters, from 2008:
- 8a, , , , , Angew. Chem. 2008, 120, 2492;Angew. Chem. Int. Ed. 2008, 47, 2458;Direct Link:Direct Link:
- 8b, , , , , Angew. Chem. 2008, 120, 2882;Angew. Chem. Int. Ed. 2008, 47, 2840;Direct Link:Direct Link:
- 8c, , Angew. Chem. 2008, 120, 3687;Angew. Chem. Int. Ed. 2008, 47, 3631;Direct Link:Direct Link:
- 8d
- 8e
- 8f
- 8g, , , , , , , J. Am. Chem. Soc. 2009, 131, 4562;
- 8h
- 8i
- 8j
- 8k
- 8l
- 8m
- 8n
- 8o
- 8p
- 8q, , , Angew. Chem. 2009, 121, 4290;Angew. Chem. Int. Ed. 2009, 48, 4226;Direct Link:Direct Link:
- 8r, , , Angew. Chem. 2009, 121, 2591;Angew. Chem. Int. Ed. 2009, 48, 2553;Direct Link:Direct Link:
- 8s, , , , , Angew. Chem. 2009, 121, 6845;Angew. Chem. Int. Ed. 2009, 48, 6717;Direct Link:Direct Link:
- 8t
- 8u, , , Angew. Chem. 2009, 121, 7564;Angew. Chem. Int. Ed. 2009, 48, 7428;Direct Link:Direct Link:
- 8v
- 8w
- 9Selected examples on asymmetric catalysis employing BINOL phosphoric acids from our laboratory:
- 9a, , , Angew. Chem. 2006, 118, 2679;Angew. Chem. Int. Ed. 2006, 45, 2617;Direct Link:Direct Link:
- 9b, , Angew. Chem. 2006, 118, 7996;Angew. Chem. Int. Ed. 2006, 45, 7832;Direct Link:Direct Link:
- 9c
- 9d
- 9e
- 9f, , , Angew. Chem. 2007, 119, 7027;Angew. Chem. Int. Ed. 2007, 46, 6903;Direct Link:Direct Link:
- 9g
- 9h, , , , Angew. Chem. 2008, 120, 603;Angew. Chem. Int. Ed. 2008, 47, 593;Direct Link:Direct Link:
- 9i, , Angew. Chem. 2008, 120, 5920;Angew. Chem. Int. Ed. 2008, 47, 5836;Direct Link:Direct Link:
- 9j, , , , Angew. Chem. 2008, 120, 6903;Angew. Chem. Int. Ed. 2008, 47, 6798;Direct Link:Direct Link:
- 9k, , Angew. Chem. 2008, 120, 10244;Angew. Chem. Int. Ed. 2008, 47, 10090;Direct Link:Direct Link:
- 9l, , , , Angew. Chem. 2009, 121, 925;Angew. Chem. Int. Ed. 2009, 48, 908;Direct Link:Direct Link:
- 9m
- 10For reviews on organocatalytic transfer hydrogenation with Hantzsch esters, see:
- 10a
- 10b
- 10c
- 10d
- 11For asymmetric Brønsted acid catalyzed transfer hydrogenations, see:
- 11a
- 11b
- 11c, , , Angew. Chem. 2005, 117, 7590;Angew. Chem. Int. Ed. 2005, 44, 7424;Direct Link:Direct Link:
- 11d
- 11e
- 11f
- 11g, , , Angew. Chem. 2006, 118, 3765;Angew. Chem. Int. Ed. 2006, 45, 3683;Direct Link:Direct Link:
- 11h, , , Angew. Chem. 2006, 118, 6903;Angew. Chem. Int. Ed. 2006, 45, 6751;Direct Link:Direct Link:
- 11i
- 11j, , Angew. Chem. 2007, 119, 4646;Angew. Chem. Int. Ed. 2007, 46, 4562;Direct Link:Direct Link:
- 11k
- 11l, , , Angew. Chem. 2008, 120, 771;Angew. Chem. Int. Ed. 2008, 47, 759;Direct Link:Direct Link:
- 11m
- 11n, , Angew. Chem. 2008, 120, 5920;Angew. Chem. Int. Ed. 2008, 47, 5836;Direct Link:Direct Link:
- 11o
- 11p
- 11q
- 11r
- 11s
- 11t
- 11u
- 12A detailed experimental procedure is given in the Supporting Information.

1615-4169/asset/2258_left.gif?v=1&s=480b85eb3acd0e8f47639c75e9ec7a59d53cd074)
