Abstract
A concise synthesis of two imidazolium ion-tagged prolinamide organocatalysts 3 and 4, varying in anionic component (CF3COO− and PF6 −, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF6 − anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented.
Graphical Abstract
Similar content being viewed by others
References
Dondoni A, Massi A (2008) Angew Chem Int Ed 47:4638–4660
Gaunt MJ, Johansson CC, McNally A, Vo NT (2007) Drug Discov Today 12:8–27
Pellissier H (2007) Tetrahedron 63:9267–9331
List B, Lerner RA, Barbas CF III (2000) J Am Chem Soc 122:2395–2396
Mukherjee S, Yang JW, Hoffmann S, List B (2007) Chem Rev 107:5471–5569
Chen XH, Yu J, Gong LZ (2010) Chem Commun 46:6437–6448
Lo CM, Chow HF (2009) J Org Chem 74:5181–5191
Moorthy JN, Saha S (2010) Eur J Org Chem 2010:6359–6365
Tian H, Gao J-L, Xu H, Zheng L-Y, Huang W-B, Liu Q-W, Zhang S-Q (2011) Tetrahedron Asymmetry 22:1074–1080
Guizzetti S, Benaglia M, Pignataro L, Puglisi A (2006) Tetrahedron Asymmetry 17:2754–2760
Akagawa K, Sakamoto S, Kudo K (2005) Tetrahedron Lett 46:8185–8187
Alza E, Sayalero S, Kasaplar P, Almasi D, Pericas MA (2011) Chem Eur J 17:11585–11595
Goren K, Portnoy M (2010) Chem Commun 46:1965–1967
Li P, Wang L, Zhang Y, Wang G (2008) Tetrahedron 64:7633–7638
Miranda PO, Lizandara-Pueyo C, Pericàs MA (2013) J Catal 305:169–178
Kochetkov SV, Kucherenko AS, Kryshtal GV, Zhdankina GM, Zlotin SG (2012) Eur J Org Chem 2012:7129–7134
Kucherenko AS, Siyutkin DE, Nigmatov AG, Chizhov AO, Zlotin SG (2012) Adv Synth Catal 354:3078–3086
Larionova NA, Kucherenko AS, Siyutkin DE, Zlotin SG (2011) Tetrahedron 67:1948–1954
Maltsev OV, Chizhov AO, Zlotin SG (2011) Chem Eur J 17:6109–6117
Maltsev OV, Kucherenko AS, Zlotin SG (2011) Mendeleev Commun 21:146–148
Siyutkin DE, Kucherenko AS, Frolova LL, Kuchin AV, Zlotin SG (2011) Tetrahedron Asymmetry 22:1320–1324
Siyutkin DE, Kucherenko AS, Frolova LL, Kuchin AV, Zlotin SG (2013) Tetrahedron Asymmetry 24:776–779
Siyutkin DE, Kucherenko AS, Struchkova MI, Zlotin SG (2008) Tetrahedron Lett 49:1212–1216
Siyutkin DE, Kucherenko AS, Zlotin SG (2009) Tetrahedron 65:1366–1372
Siyutkin DE, Kucherenko AS, Zlotin SG (2010) Tetrahedron 66:513–518
Lombardo M, Easwar S, Pasi F, Trombini C (2009) Adv Synth Catal 351:276–282
Miao W, Chan TH (2006) Adv Synth Catal 348:1711–1718
Khan SS, Shah J, Liebscher J (2011) Tetrahedron 67:1812–1820
Liebscher J, Shah J, Khan S, Blumenthal H (2009) Synthesis 2009:3975–3982
Brozinski HL, Delaney JP, Henderson LC (2013) Aust J Chem 66:844
Li J, Liu L (2013) Synth Commun 43:476–485
Luo S, Mi X, Zhang L, Liu S, Xu H, Cheng JP (2006) Angew Chem Int Ed 45:3093–3097
Ni B, Zhang Q, Headley AD (2008) Tetrahedron Lett 49:1249–1252
Hunt PA, Kirchner B, Welton T (2006) Chem Eur J 12:6762–6775
Izgorodina EI, MacFarlane DR (2011) J Phys Chem B 115:14659–14667
Delaney JP, Brozinski HL, Henderson LC (2013) Org Biomol Chem 11:2951–2960
Delaney JP, Henderson LC (2011) Int J Mol Sci 12:9083–9094
Delaney JP, Henderson LC (2012) Adv Synth Catal 354:197–204
Aratake S, Itoh T, Okano T, Usui T, Shoji M, Hayashi Y (2007) Chem Commun 24:2524–2526
Giorgi G, López-Alvarado P, Miranda S, Rodriguez J, Menéndez JC (2013) Eur J Org Chem 2013:1327–1336
Gruttadauria M, Giacalone F, Noto R (2009) Adv Synth Catal 351:33–57
Hayashi Y (2006) Angew Chem Int Ed 45:8103–8104
Jung Y, Marcus RA (2007) J Am Chem Soc 129:5492–5502
Mase N, Barbas CF III (2010) Org Biomol Chem 8:4043–4050
Tzeng Z-H, Chen H-Y, Huang C-T, Chen K (2008) Tetrahedron Lett 49:4134–4137
Beattie JK, McErlean CS, Phippen CB (2010) Chem Eur J 16:8972–8974
Mlynarski J, Paradowska J (2008) Chem Soc Rev 37:1502–1511
Raj M, Singh VK (2009) Chem Commun 44:6687–6703
Simon MO, Li CJ (2012) Chem Soc Rev 41:1415–1427
Li P, Wang L, Wang M, Zhang Y (2008) Eur J Org Chem 2008:1157–1160
Luo S, Mi X, Zhang L, Liu S, Xu H, Cheng J-P (2006) Angew Chem Int Ed 45:3093–3097
Lin J, Tian H, Jiang Y-J, Huang W-B, Zheng L-Y, Zhang S-Q (2011) Tetrahedron Asymmetry 22:1434–1440
Lu A, Liu T, Wu R, Wang Y, Zhou Z, Wu G, Fang J, Tang C (2010) Eur J Org Chem 2010(30):5777–5781
Zhong J, Guan Z, He Y-H (2013) Catal Commun 32:18–22
Lin J, Tian H, Jiang Y-J, Huang W-B, Zheng L-Y, Zhang S-Q (2011) Tetrahedron Asymmetry 22:1434–1440
Sanchez D, Bastida D, Bures J, Isart C, Pineda O, Vilarrasa J (2012) Org Lett 14(2):536–539
Acknowledgments
The authors acknowledge the Institute for Frontier Materials, Strategic Research Centre for Chemistry and Biotechnology, and the Faculty of Science, Engineering, and Built Environment for funding. We acknowledge the Institute for Frontier Materials for the postgraduate scholarship to DE.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Eyckens, D.J., Brozinski, H.L., Delaney, J.P. et al. Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water. Catal Lett 146, 212–219 (2016). https://doi.org/10.1007/s10562-015-1630-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-015-1630-4