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Journal
2014 | 12 | 3 | 416-425
Article title

Enantioselective Michael additions of aldehydes to nitroalkenes catalyzed with ionically tagged organocatalyst

Content
Title variants
Languages of publication
EN
Abstracts
EN
Enantioselective organocatalytic Michael additions affords useful building blocks for many biologically and medicinally relevant compounds. Ionically-tagged diphenylprolinol silyl ether efficiently catalyzes several Michael additions of aldehydes to nitroalkenes in ionic liquids. The Michael additions work well in ionic liquids; yields up to 95% and enantioselectivities up to 95% ee were achieved. Furthermore, in some cases, the catalytic system was reusable.
Publisher

Journal
Year
Volume
12
Issue
3
Pages
416-425
Physical description
Dates
published
1 - 3 - 2014
online
21 - 12 - 2013
Contributors
author
  • Synkola
References
  • [1] A. Berkessel, H. Gröger, Asymmetric Organocatalysis (Wiley-VCH, Weinheim, Germany, 2005) http://dx.doi.org/10.1002/3527604677[Crossref]
  • [2] P.I. Dalko, Asymmetric Organocatalysis: Reactions and Experimental Procedures (Wiley-VCH, Weinheim, 2007)
  • [3] B. List, Asymmetric Organocatalysis (Springer, Heidelberg, 2009) http://dx.doi.org/10.1007/978-3-642-02815-1[Crossref]
  • [4] H. Pellissier, Recent Developments in Asymmetric Organocatalysis (RSC Publishing, Cambridge, 2012)
  • [5] R. Šebesta (Ed.), Enantioselective Homogeneous Supported Catalysis (The Royal Society of Chemistry, Cambridge, 2012)
  • [6] Š. Toma, In: R. Šebesta (Ed.), Enantioselective Homogeneous Supported Catalysis (The Royal Society of Chemistry, Cambridge, 2012) 18–57
  • [7] M. Benaglia, In: M. Benaglia (Ed.), Recoverable and Recyclable Catalysts (John Wiley & Sons, Chichester, 2009) 301–340
  • [8] Š. Toma, M. Mečiarová, R. Šebesta, Eur. J. Org. Chem. 321 (2009)
  • [9] J.G. Hernández, E. Juaristi, Chem. Commun. 48, 5396 (2012) http://dx.doi.org/10.1039/c2cc30951c[Crossref]
  • [10] Š. Toma, R. Šebesta, In: P. Domínguez de María (Ed.), Ionic Liquids in Biotransformations and Organocatalysis (John Wiley & Sons, Hoboken, 2012) 331–359
  • [11] R. Šebesta, I. Kmentová, Š. Toma, Green Chem. 10, 484 (2008) http://dx.doi.org/10.1039/b801456f[Crossref]
  • [12] S. Luo, L. Zhang, J.-P. Cheng, Chem. Asian J. 4, 1184 (2009) http://dx.doi.org/10.1002/asia.200900080[Crossref]
  • [13] M. Lombardo, C. Trombini, ChemCatChem 2, 135 (2010) http://dx.doi.org/10.1002/cctc.200900256[Crossref]
  • [14] D. Almasi, D.A. Alonso, C. Nájera, Tetrahedron: Asymmetry 18, 299 (2007)
  • [15] S. Sulzer-Mosse, A. Alexakis, Chem. Commun. 3123 (2007)
  • [16] J.L. Vicario, D. Badia, L. Carrillo, Synthesis 2065 (2007)
  • [17] S.B. Tsogoeva, Eur. J. Org. Chem. 1701 (2007)
  • [18] O.V. Maltsev, I.P. Beletskaya, S.G. Zlotin, Russ. Chem. Rev. 80, 1067 (2011) http://dx.doi.org/10.1070/RC2011v080n11ABEH004249[Crossref]
  • [19] Y. Zhang, W. Wang, Catal. Sci. Technol. 2, 42–53 (2012) http://dx.doi.org/10.1039/c1cy00334h[Crossref]
  • [20] D. Enders, C. Wang, J.X. Liebich, Chem. Eur. J. 15, 11058 (2009) http://dx.doi.org/10.1002/chem.200902236[Crossref]
  • [21] D. Enders, K. Luttgen, A.A. Narine, Synthesis 959 (2007)
  • [22] D. Enders, C. Grondal, M.R. M. Huttl, Angew. Chem. Int. Ed. 46, 1570 (2007) http://dx.doi.org/10.1002/anie.200603129[Crossref]
  • [23] X. Yu, W. Wang, Org. Biomol. Chem. 6, 2037 (2008) http://dx.doi.org/10.1039/b800245m[Crossref]
  • [24] C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2, 167 (2010) http://dx.doi.org/10.1038/nchem.539[Crossref]
  • [25] H. Pellissier, Adv. Synth. Catal. 354, 237 (2012) http://dx.doi.org/10.1002/adsc.201100714[Crossref]
  • [26] R. Marcia de Figueiredo, M. Christmann, Eur. J. Org. Chem. 2575 (2007)
  • [27] J. Aleman, S. Cabrera, Chem. Soc. Rev. 42, 774 (2013) http://dx.doi.org/10.1039/c2cs35380f[Crossref]
  • [28] M. Marigo, T.C. Wabnitz, D. Fielenbach, K.A. Jørgensen, Angew. Chem. Int. Ed. 44, 794 (2005) http://dx.doi.org/10.1002/anie.200462101[Crossref]
  • [29] Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. Int. Ed. 44, 4212 (2005) http://dx.doi.org/10.1002/anie.200500599[Crossref]
  • [30] A. Mielgo, C. Palomo, Chem. Asian J. 3, 922 (2008) http://dx.doi.org/10.1002/asia.200700417[Crossref]
  • [31] K.L. Jensen, G. Dickmeiss, H. Jiang, Ł. Albrecht, K.A. Jørgensen, Acc. Chem. Res. 45, 248 (2011) http://dx.doi.org/10.1021/ar200149w[Crossref]
  • [32] G.-L. Zhao, J. Vesely, J. Sun, K.E. Christensen, C. Bonneau, A. Córdova, Adv. Synth. Catal. 350, 657 (2008) http://dx.doi.org/10.1002/adsc.200700570[Crossref]
  • [33] P. García-García, A. Ladépęche, R. Halder, B. List, Angew. Chem. Int. Ed. 47, 4719 (2008) http://dx.doi.org/10.1002/anie.200800847[Crossref]
  • [34] S. Belot, A. Massaro, A. Tenti, A. Mordini, A. Alexakis, Org. Lett. 10, 4557 (2008) http://dx.doi.org/10.1021/ol801772p[Crossref]
  • [35] R.-S. Luo, J. Weng, H.-B. Ai, G. Lu, A.S.C. Chan, Adv. Synth. Catal. 351, 2449 (2009) http://dx.doi.org/10.1002/adsc.200900355[Crossref]
  • [36] B. Han, Y.-C. Xiao, Z.-Q. He, Y.-C. Chen, Org. Lett. 11, 4660 (2009) http://dx.doi.org/10.1021/ol901939b[Crossref]
  • [37] L. Wang, X. Zhang, D. Ma, Tetrahedron 68, 7675 (2012) http://dx.doi.org/10.1016/j.tet.2012.05.088[Crossref]
  • [38] A. Landa, M. Maestro, C. Masdeu, Á. Puente, S. Vera, M. Oiarbide, C. Palomo, Chem. Eur. J. 15, 1562 (2009) http://dx.doi.org/10.1002/chem.200802441[Crossref]
  • [39] Q. Zhu, Y. Lu, Org. Lett. 10, 4803 (2008) http://dx.doi.org/10.1021/ol8019296[Crossref]
  • [40] S. Zhu, Y. Wang, D. Ma, Adv. Synth. Catal. 351, 2563 (2009) http://dx.doi.org/10.1002/adsc.200900449[Crossref]
  • [41] O.V. Maltsev, A.S. Kucherenko, S.G. Zlotin, Eur. J. Org. Chem. 5134 (2009)
  • [42] M. Lombardo, M. Chiarucci, A. Quintavalla, C. Trombini, Adv. Synth. Catal. 351, 2801 (2009) http://dx.doi.org/10.1002/adsc.200900599[Crossref]
  • [43] S.K. Ghosh, Y. Qiao, B. Ni, A.D. Headley, Org. Biomol. Chem. 11, 1801 (2013) http://dx.doi.org/10.1039/c3ob27398a[Crossref]
  • [44] S.K. Ghosh, K. Dhungana, A.D. Headley, B. Ni, Org. Biomol. Chem. 10, 8322 (2012) http://dx.doi.org/10.1039/c2ob26248g[Crossref]
  • [45] J. Rehák, M. Huťka, A. Latika, H. Brath, A. Almássy, V. Hajzer, J. Durmis, S. Toma, R. Šebesta, Synthesis 44, 2424 (2012) http://dx.doi.org/10.1055/s-0031-1290396[Crossref]
  • [46] K. Patora-Komisarska, M. Benohoud, H. Ishikawa, D. Seebach, Y. Hayashi, Helv. Chim. Acta 94, 719 (2011) http://dx.doi.org/10.1002/hlca.201100122[Crossref]
  • [47] H. Ishikawa, T. Suzuki, Y. Hayashi, Angew. Chem. Int. Ed. 48, 1304 (2009) http://dx.doi.org/10.1002/anie.200804883[Crossref]
  • [48] S. Zhu, S. Yu, Y. Wang, D. Ma, Angew. Chem. Int. Ed. 49, 4656 (2010) http://dx.doi.org/10.1002/anie.201001644[Crossref]
  • [49] V. Hajzer, A. Latika, J. Durmis, R. Šebesta, Helv. Chim. Acta 95, 2421 (2012) http://dx.doi.org/10.1002/hlca.201200527[Crossref]
  • [50] M.H. Haindl, M.B. Schmid, K. Zeitler, R.M. Gschwind, RSC Adv. 2, 5941 (2012) http://dx.doi.org/10.1039/c2ra20860a[Crossref]
  • [51] H. Ishikawa, T. Suzuki, H. Orita, T. Uchimaru, Y. Hayashi, Chem. Eur. J. 16, 12616 (2010) http://dx.doi.org/10.1002/chem.201001108[Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-013-0391-4
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