A Snapshot of Ionic-Liquid-Tagged Proline-Based Organocatalysts
Hannah L. Brozinski A , Joshua P. Delaney A and Luke C. Henderson A B C
+ Author Affiliations
- Author Affiliations
A Strategic Research Center for Chemistry and Biotechnology, Deakin University, Pigdons Road, Geelong, Vic. 3216, Australia.
B Institute for Frontier Materials, Deakin University, Pigdons Road, Geelong, Vic. 3216, Australia.
C Corresponding author. Email: luke.henderson@deakin.edu.au
Australian Journal of Chemistry 66(8) 844-847 https://doi.org/10.1071/CH13218
Submitted: 29 April 2013 Accepted: 27 June 2013 Published: 31 July 2013
Abstract
This highlight focuses on the developments in ionic-liquid (IL)-tagged proline-based organocatalysts. An overview of catalyst structure and application to asymmetric transformations is provided, and a representative synthesis of an IL-tagged organocatalyst is also discussed.
References
[1] B. List, R. A. Lerner, C. F. Barbas, J. Am. Chem. Soc. 2000, 122, 2395.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXhtlGqurk%3D&md5=79c01b9061838d376912945d02063796CAS |
[2] K. L. Jensen, G. Dickmiess, H. Jiuang, Ł. Albrecht, K. A. Jørgensen, Acc. Chem. Res. 2012, 45, 248.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVemu7zO&md5=9e109cda77fde8bd5f29287eb7d6f06fCAS | 21848275PubMed |
[3] K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXisVGjurw%3D&md5=207e90af843218e8f49b7858feceae6bCAS |
[4] J. Mlynarski, B. Gut, Chem. Soc. Rev. 2012, 41, 587.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvFGqtg%3D%3D&md5=b2c286c6512e84b3758118e0bed19115CAS | 21796310PubMed |
[5] B. List, Chem. Rev. 2007, 107, 5413.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVSqsL3I&md5=73bc90d788d020084092d2bbb84ee877CAS |
[6] Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVSlsLfJ&md5=c4d48e4680e383601c79637f92de17beCAS | 19690751PubMed |
[7] G. Guillena, C. Nájera, D. J. Ramón, Tetrahedron Asymmetr. 2007, 18, 2249.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1Smt7zO&md5=68f13af560b65f4d54ef8b324205f464CAS |
[8] J. Mlynarski, J. Paradowska, Chem. Soc. Rev. 2008, 37, 1502.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXoslOgtLk%3D&md5=4a700d5a5cb309e0d4fe3e58cbf9b247CAS | 18648676PubMed |
[9] S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVSqsLrP&md5=de6f212aaf83049fbc4137ea5c52ce86CAS | 18072803PubMed |
[10] T. E. Kristensen, T. Hansen, Eur. J. Org. Chem. 2010, 3179.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmvFejtLs%3D&md5=c2622164623c2b63218156ec53cf4ea4CAS |
[11] J. Yan, L. Wang, Chirality 2009, 21, 413.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXltFaqsL0%3D&md5=90dabbfd6275565ca10e5ca5c106e29eCAS | 18570310PubMed |
[12] A. V. Malkov, M. Figlus, G. Cooke, S. T. Caldwell, G. Rabani, M. R. Prestly, P. Kocovský, Org. Biomol. Chem. 2009, 7, 1878.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXksV2itr0%3D&md5=205183cccd4fd0e8c2f042245a6f3e45CAS | 19590783PubMed |
[13] R. Sebesta, I. Kmentov, S. Toma, Green Chem. 2008, 10, 484.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXltFyjsrg%3D&md5=d7640a004b45b49a2c7eea48933d955cCAS |
[14] S. S. Khan, J. Shah, J. Liebscher, Tetrahedron 2011, 67, 1812.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhvFChu7w%3D&md5=d440e35a08782397f6853600cc859f97CAS |
[15] D. E. Siyutkin, A. S. Kucherenko, S. G. Zlotin, Tetrahedron 2010, 66, 513.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFGntb3J&md5=247c72299ec44aa4be518367db92ee63CAS |
[16] W. Miao, T. H. Chan, Adv. Synth. Catal. 2006, 348, 1711.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XovFyms74%3D&md5=984390a4a6bf3dad5c8098d305785255CAS |
[17] X. Ding, W. Tang, C. Zhu, Y. Cheng, Adv. Synth. Catal. 2010, 352, 108.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFanu7s%3D&md5=d3cce4824b0b14cc7840ab1f88ef2e3aCAS |
[18] O. V. Maltsev, A. S. Kucherenko, I. P. Beletskaya, V. A. Tartakovsky, S. G. Zlotin, Eur. J. Org. Chem. 2010, 2927.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmt1eju7c%3D&md5=cd72b529fe53d353266e598779a059bbCAS |
[19] O. V. Maltsev, A. S. Kucherenko, S. G. Zlotin, Eur. J. Org. Chem. 2009, 5134.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1KjurjL&md5=bcfc028f1f6541be2360d21cdb9c69deCAS |
[20] O. V. Maltsev, A. S. Kucherenko, A. L. Chimishkyan, S. G. Zlotin, Tetrahedron Asymmetr. 2010, 21, 2659.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsFehurzK&md5=cdfb434fe8806d17a84ab16e0b6702edCAS |
[21] S. V. Kochetkov, A. S. Kucherenko, G. A. Kryshtal, G. M. Zhdankina, S. G. Zlotin, Eur. J. Org. Chem. 2012, 7129.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhs1agsbzP&md5=c2ab396ea66d4a23d7b9089c7a17fcebCAS |
[22] D. E. Siyutkin, A. S. Kucherenko, M. Struchkova, S. G. Zlotin, Tetrahedron Lett. 2008, 49, 1212.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXosFansA%3D%3D&md5=7fe415da9fafef93c16053f9d3530e02CAS |
[23] M. Lombardo, S. Easwar, F. Pasi, C. Trombini, Adv. Synth. Catal. 2009, 351, 276.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhvVWktL0%3D&md5=974211a7a9f1dc90d24b9fb178e05bccCAS |
[24] M. Lombardo, S. Easwar, F. Pasi, C. Trombini, Adv. Synth. Catal. 2007, 349, 2061.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVels7bP&md5=009c03be6b48208c93db1b91e082e1efCAS |
[25] J. Shah, S. S. Khan, H. Blumenthal, J. Liebsher, Synthesis 2009, 23, 3975.
[26] S. S. Khan, J. Shah, J. Liebsher, Tetrahedron 2010, 66, 5082.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXntVyqurk%3D&md5=bc854b28dfa1b9fbdbb799fd06287a47CAS |
[27] X. Ding, H.-L. Jiang, C.-J. Zhu, Y.-X. Cheng, Tetrahedron Lett. 2010, 51, 6105.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlentrvJ&md5=a3c391024babf5d308062a8ea914f94dCAS |
[28] J. Franzen, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1KktrjF&md5=09a0d6133e55e14c98944f796d33b1ecCAS | 16366584PubMed |
[29] J. P. Delaney, L. C. Henderson, Adv. Synth. Catal. 2012, 354, 197.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xmt1Krsw%3D%3D&md5=2410fe4a000c0a9ec3b99caa26adba9aCAS |
[30] J. P. Delaney, L. C. Henderson, Int. J. Mol. Sci. 2011, 12, 9083.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XptF2juw%3D%3D&md5=2dfb5f52ed27bd7d8617e58215039e7fCAS | 22272120PubMed |
[31] J. P. Delaney, H. L. Brozinski, L. C. Henderson, Org. Biomol. Chem. 2013, 11, 2951.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXmtVWksL4%3D&md5=e791a0b5d807ad496f9b2707a8ed13b3CAS | 23455677PubMed |
[32] S. Samanta, J. Liu, R. Dodda, C.-G. Zhao, Org. Lett. 2005, 7, 5321.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVKmtb%2FP&md5=5d4921f1a6f49088d49f593fa96f88ceCAS | 16268568PubMed |
[33] G. Guillena, M. C. Hita, C. Najera, Tetrahedron Asymmetr. 2006, 17, 1493.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xms1aitL0%3D&md5=01bd354d92ad58d9f5efb53530df9cb7CAS |
[34] A. S. Kucherenko, D. E. Siyutkin, A. G. Nigmatov, A. O. Chizhov, S. G. Zlotin, Adv. Synth. Catal. 2012, 354, 3078.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhs1ags7vO&md5=31a814eca2bbad1a86aabafb18be38d9CAS |
[35] D. E. Siyutkin, A. S. Kucherenko, S. G. Zlotin, Tetrahedron 2009, 65, 1366.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXptl2gtA%3D%3D&md5=6af2da3081f1bbcc13ff49b155424975CAS |
[36] Z.-L. Shen, K. K. K. Goh, C. H. A. Wong, W.-Y. Loo, Y.-S. Yang, J. Lu, T.-P. Loh, Chem. Commun. 2012, 48, 5856.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xnt1ert7k%3D&md5=9d1317f4df547484d60cb0463c66ba7aCAS |
