1-Naphthyl-TADDOL/Emim BF4: A new catalytic system for the asymmetric addition of Chan’s diene to aromatic aldehydes

• Authors: Rosaria Villano , Maria Acocella , Vincenzo Sio , Arrigo Scettri
• Languages of publication: EN

Abstracts

EN

A new organocatalytic system was tested as a promoter for the asymmetric addition of Chan’s diene to aldehydes under solvent-free conditions. This new organocatalyst generated in situ by mixing 1-naphthyl-TADDOL derivative and Emim BF4 was able to give enantioenriched vinylogous aldols and hetero-Diels-Alder cycloadducts. A mechanistic investigation through the detection of nonlinear effects confirmed the involvement of the ionic liquid in the formation of a new catalytic supramolecular species.

Keywords

EN

Organocatalysis; Hydrogen bonding; Chan’s diene; Aldol reaction; Cycloaddition

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 6
• Pages: 1172-1178

Dates

published

1 - 12 - 2010

online

8 - 10 - 2010

Contributors

author

Rosaria Villano

• Institute of Biomolecular Chemistry — CNR, Reg. Baldinca, 07040, Li Punti (Sassari), Italy

author

Maria Acocella

• Department of Chemistry, University of Salerno, 84084, Fisciano (Salerno), Italy

author

Vincenzo Sio

• Department of Chemistry, University of Salerno, 84084, Fisciano (Salerno), Italy

author

Arrigo Scettri

• Department of Chemistry, University of Salerno, 84084, Fisciano (Salerno), Italy

References

• [1] D. Seebach, A.K. Beck, A. Heckel, Angew. Chem. Int. Ed. 40, 92 (2001) http://dx.doi.org/10.1002/1521-3773(20010105)40:1<92::AID-ANIE92>3.0.CO;2-K[Crossref]
• [2] H. Pellissier, Tetrahedron 64, 10279 (2008) and references cited therein http://dx.doi.org/10.1016/j.tet.2008.08.029[Crossref]
• [3] A.N. Thadani, A.R. Stankovic, V.H. Rawal, Proc. Natl. Acad. Sci. USA 101, 5846 (2004) http://dx.doi.org/10.1073/pnas.0308545101[Crossref]
• [4] Y. Huang, A.K. Unni, A.N. Thadani, V.H. Rawal, Nature 424, 146 (2003) http://dx.doi.org/10.1038/424146a[Crossref]
• [5] H. Du, D. Zhao, K. Ding, Chem. Eur. J. 10, 5964 (2004) http://dx.doi.org/10.1002/chem.200400515[Crossref]
• [6] T. Tonoi, K. Mikami, Tetrahedron Lett. 46, 6355 (2005) http://dx.doi.org/10.1016/j.tetlet.2005.07.043[Crossref]
• [7] X. Zhang, H. Du, Z. Wang, Y.-D. Wu, K. Ding, J. Org. Chem. 71, 2862 (2006) http://dx.doi.org/10.1021/jo060129c[Crossref]
• [8] R. Villano, M.R. Acocella, A. Massa, L. Palombi, A. Scettri, Tetrahedron Lett. 48, 891 (2007) http://dx.doi.org/10.1016/j.tetlet.2006.11.159[Crossref]
• [9] M. Rueping, E. Sugiono, S.A. Moreth, Adv. Synth. Catal. 349 759 (2007) http://dx.doi.org/10.1002/adsc.200600405[Crossref]
• [10] A.K. Unni, N. Takenaka, H. Yamamoto, V.H. Rawal, J. Am. Chem. Soc. 127, 1336 (2005) http://dx.doi.org/10.1021/ja044076x[Crossref]
• [11] M. Kalesse, Top. Curr. Chem. 244, 43 (2005)
• [12] G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 100, 1929 (2000). http://dx.doi.org/10.1021/cr990247i[Crossref]
• [13] A. Soriente, M. De Rosa, R. Villano, A. Scettri, Curr. Org. Chem. 8, 993 (2004) http://dx.doi.org/10.2174/1385272043370212[Crossref]
• [14] S.E. Denmark, J.R. Heemstra Jr, G.L. Beutner, Angew. Chem. Int. Ed. 44, 4682 (2005) http://dx.doi.org/10.1002/anie.200462338[Crossref]
• [15] V.B. Gondi, M. Gravel, V.H. Rawal, Org. Lett. 7, 5657 (2005) http://dx.doi.org/10.1021/ol052301p[Crossref]
• [16] A. Soriente, M. De Rosa, M. Stanzione, R. Villano, A. Scettri, Tetrahedron: Asymmetry 12, 959 (2001) http://dx.doi.org/10.1016/S0957-4166(01)00150-1[Crossref]
• [17] A. Soriente, M. De Rosa, R. Villano, A. Scettri, Tetrahedron: Asymmetry 11, 2255 (2000) http://dx.doi.org/10.1016/S0957-4166(00)00200-7[Crossref]
• [18] D.A. Evans, M.C. Kozlowski, J.A. Murry, C.S. Burgey, K.R. Campos, B.T. Connell, R.J. Staples, J. Am. Chem. Soc. 121, 669 (1999) http://dx.doi.org/10.1021/ja9829822[Crossref]
• [19] D.A. Evans, J.A. Murry, M.C. Kozlowski, J. Am. Chem. Soc. 118, 5814 (1996) http://dx.doi.org/10.1021/ja960712i[Crossref]
• [20] R. Giernoth, Top. Curr. Chem. 276, 1 (2007) http://dx.doi.org/10.1007/128_016[Crossref]
• [21] H. Olivier-Bourbigou, L. Magna, D. Morvan, Applied Catalysis A: General 373, 1 (2010) http://dx.doi.org/10.1016/j.apcata.2009.10.008[Crossref]
• [22] J. Muzart, Adv. Synth. Catal. 348, 275 (2006) http://dx.doi.org/10.1002/adsc.200505273[Crossref]
• [23] C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, J.-C. Plaquevent, Tetrahedron: Asymmetry 14, 3081 (2003) http://dx.doi.org/10.1016/S0957-4166(03)00596-2[Crossref]
• [24] M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108, 2015 (2008) http://dx.doi.org/10.1021/cr078399y[Crossref]
• [25] V.I. Pârvulescu, C. Hardacre, Chem. Rev. 107, 2615 (2007) http://dx.doi.org/10.1021/cr050948h[Crossref]
• [26] M.J. Earle, S.P. Katdare, K.R. Seddon, Org. Lett. 6, 707 (2004) http://dx.doi.org/10.1021/ol036310e[Crossref]
• [27] B.K. Liu, Q. Wu, J.M. Wu, L. Xian-Fu, Chem. Commun., 295 (2007) [Crossref]
• [28] W.Y. Lou, M.H. Zong, H. Wu, R. Xu, J.F. Wang, Green Chem. 7, 500 (2005) http://dx.doi.org/10.1039/b502716k[Crossref]
• [29] T. Itoh, S. Han, Y. Matsushita, S. Hayase, Green Chem. 6, 437 (2004) http://dx.doi.org/10.1039/b405396f[Crossref]
• [30] K.M. Dieter, C.J. Dymek Jr, N.E. Heimer, J.W. Rovang, J.S. Wilkes, J. Am. Chem. Soc. 110, 2722 (1988) http://dx.doi.org/10.1021/ja00217a004[Crossref]
• [31] J. Howarth, K. Hanlon, D. Fayne, P. McCormac, Tetrahedron Lett. 38, 3097 (1997) http://dx.doi.org/10.1016/S0040-4039(97)00554-6[Crossref]
• [32] E.J. Kim, S.Y. Ko, C.E. Song, Helv. Chim. Acta 86, 894 (2003) http://dx.doi.org/10.1002/hlca.200390087[Crossref]
• [33] A. Aggarwal, N.L. Lancaster, A.R. Sethi, T. Welton, Green Chem. 4, 517 (2002) http://dx.doi.org/10.1039/b206472c[Crossref]
• [34] J.N. Rosa, C.A.M. Afonso, A.G. Santos, Tetrahedron 57, 4189 (2001) http://dx.doi.org/10.1016/S0040-4020(01)00316-7[Crossref]
• [35] R. Villano, M.R. Acocella, A. Massa, L. Palombi, A. Scettri, Tetrahedron 65, 5571 (2009) http://dx.doi.org/10.1016/j.tet.2009.01.112[Crossref]
• [36] T. Satyanarayana, S. Abraham, H.B. Kagan, Angew. Chem. Int. Ed. 48, 456 (2009) http://dx.doi.org/10.1002/anie.200705241[Crossref]
• [37] C. Girard, H.B. Kagan, Angew. Chem. Int. Ed. 37, 2922 (1998) http://dx.doi.org/10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO;2-1[Crossref]
• [38] K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. Int. Ed. 39, 3532 (2000) [Crossref]
• [39] T. Ohga, S. Umeda, Y. Kawanamai, Tetrahedron 57, 4825 (2001) http://dx.doi.org/10.1016/S0040-4020(01)00423-9[Crossref]
• [40] O. Legrand, J.-M. Brunel, G. Buono, Tetrahedron Lett. 41, 105 (2000)
• [41] P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 57, 9225 (2001) http://dx.doi.org/10.1016/S0040-4020(01)00906-1[Crossref]
• [42] S. Caddick, R. Fitzmaurice, Tetrahedron 65, 3325 (2009) http://dx.doi.org/10.1016/j.tet.2009.01.105[Crossref]
• [43] Z.Z. Zhou, F.Q. Ji, M. Cao, G.F. Yang, Adv. Synth. Catal. 348, 1826 (2006) http://dx.doi.org/10.1002/adsc.200606156[Crossref]
• [44] J.S. Yadav, K. Anuradha, B.V.S. Reddy, B. Eeshwaraiah, Tetrahedron Lett. 44, 8959 (2003) http://dx.doi.org/10.1016/j.tetlet.2003.10.015[Crossref]
• [45] S. Mossé, A. Alexakis, Org. Lett. 8, 3577 (2006) http://dx.doi.org/10.1021/ol0614727[Crossref]
• [46] M. Hosseini, N. Stiasni, V. Barbieri, C.O. Kappe, J. Org. Chem. 72, 1417 (2007) http://dx.doi.org/10.1021/jo0624187[Crossref]
• [47] D. Almasi, D.A. Alonso, E. Gómez-Bengoa, Y. Nagel, C. Nájera, Eur. J. Org. Chem., 2328 (2007) [Crossref]
• [48] B. Westermann, C. Neuhaus, Angew. Chem. It. Ed. 44, 4077 (2005) http://dx.doi.org/10.1002/anie.200500297[Crossref]
• [49] A. Massi, A. Nuzzi, A. Dondoni, J. Org. Chem. 72, 10279 (2007) http://dx.doi.org/10.1021/jo701959b[Crossref]
• [50] P. Brownbridge, T.H. Chan, M.A. Brook, G.J. Kang, Can. J. Chem. 61, 688 (1983) http://dx.doi.org/10.1139/v83-127[Crossref]
• [51] A.K. Bose, S.N. Ganguly, M.S. Manhas, W. He, J. Speck, Tetrahedron Lett. 47, 3213 (2006) http://dx.doi.org/10.1016/j.tetlet.2006.03.059[Crossref]

Identifiers

DOI

10.2478/s11532-010-0100-5