Use of Ionic Liquids as Solvents for Epoxidation Reactions Catalysed by a Chiral Katsuki-Type Salen Complex: Enhanced Reactivity and Recovery of Catalyst
Article
- 154 Downloads
- 19 Citations
Abstract
The Katsuki-type catalyst 2 has been recycled several times following its use in a model epoxidation reaction of 1,2-dihydronaphthalene in an ionic liquid, 3a or 3b. The enantioselectivity was comparable to that in dichloromethane, but recovery of the catalyst was easier, activity was higher, and activity and enantioselectivity were retained in recovered ionic liquid fractions to a much greater extent than those for the Jacobsen-type catalyst 1.
Ionic liquids Katsuki-type chiral catalyst Two-phase systems Epoxidation 1 2-dihydronaphthalene.
Preview
Unable to display preview. Download preview PDF.
References
- [1]J. F. Larrow and E. N. Jacobsen, Topics Organomet. Chem. 6 (2004) 123 and references therein.Google Scholar
- [2]T. Katsuki, Coord. Chem. Rev. 140 (1995) 189.Google Scholar
- [3]S. B. Ogunwumi and T. Bein, Chem. Commun. (1997) 901.Google Scholar
- [4]J. M. Fraile, J. I. Garcia, J. Massam and J. A. Mayoral, J. Mol. Catal. A: Chem. 136 (1998) 47.Google Scholar
- [5]K. B. M. Janssen, I. Laquiere, W. Dehaen, R. F. Parton, I. F. J. Vankelecom and P. A. Jacobs, Tetrahedron:Asymmetry 8 (1997) 3481.Google Scholar
- [6]L. Frunnza, H. Kosslick, H. Landmesser, E. Ho ¨ft and R. Fricke, J. Mol. Catal. A:Chem. 123 (1997) 179.Google Scholar
- [7]G.-J. Kim and J.-H. Shin, Tetrahedron Lett. 40 (1999) 6827.Google Scholar
- [8]B. D. De, B. B. Lohray and P. K. Dhal, Tetrahedron Lett. 34 (1993) 2371.Google Scholar
- [9]F. Minutolo, D. Pini, A. Petri and P. Salvadori, Tetrahedron: Asymmetry 7 (1996) 2293.Google Scholar
- [10]L. Canali, E. Cowan, H. Deleuze, C. L. Gibson and D. C. Sherrington, Chem. Commun. (1998) 2561.Google Scholar
- [11]L. Canali, E. Cowan, H. Deleuze, C. L. Gibson and D. C. Sherrington, J. Chem. Soc., Perkin Trans. 1 (2000) 2055.Google Scholar
- [12]T. S. Reger and K. D. Janda, J. Am. Chem. Soc. 122 (2000) 6929.Google Scholar
- [13]C. E. Song, E. J. Roh, B. M. Yu, D. Y. Chi, S. C. Kim and K.-J. Lee, Chem. Commun. (2000) 615.Google Scholar
- [14]K. Smith and C.-H. Liu, Chem. Commun. (2002) 886.Google Scholar
- [15]R. Broinbauer and E. N. Jacobsen, Angew. Chem. Int. Ed. 39 (2000) 3604.Google Scholar
- [16]C. Pozzi, M. Cavazzini, F. Cinato, F. Montanan and S. Quici, Eur. J. Org. Chem. (1999) 1947.Google Scholar
- [17]T. Welton, Chem. Rev. 99 (1999) 2071.Google Scholar
- [18]P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3772.Google Scholar
- [19]R. Sheldon, Chem. Commun. (2001) 2399.Google Scholar
- [20]C. M. Gordon, Applied Catal. A: Chem. 222 (2001) 101.Google Scholar
- [21]D. Zhao, M. Wu, Y. Kou and E. Z. Min, Catal. Today 74 (2002) 157.Google Scholar
- [22]H. Oliver-Bourbigou and L. Magna, J. Mol. Catal. A: Chem. 182 –183 (2002) 419.Google Scholar
- [23]P. Wasserscheid and T. Welton in: Ionic Liquids in Synthesis (Wiley-VCH, Weinheim, 2003).Google Scholar
- [24]S. A. Rorsyth, J. M. Pringle and D. R. MacFarlane, Aust. J. Chem. 57 (2004) 113.Google Scholar
- [25]N. Brausch, A. Metlen and P. Wasserscheid, Chem. Commun. (2004) 1552.Google Scholar
- [26]C. E. Song, Chem. Commun. (2004) 1033.Google Scholar
- [27]C. E. Song and E. J. Roh, Chem. Commun. (2000) 837.Google Scholar
- [28]K. Smith, S. Lock, G. A. El-Hiti, M. Wada and N. Miyoshi, Org. Biomol. Chem. 2 (2004) 935.Google Scholar
- [29]K. Smith, S. D. Roberts and G. A. El-Hiti, Org. Biomol. Chem. 1 (2003) 1552.Google Scholar
- [30]K. Smith, G. A. El-Hiti, A. Jayne and M. Butters, Org. Biomol. Chem. 1 (2003) 1560.Google Scholar
- [31]K. Smith, G. A. El-Hiti, A. Jayne and M. Butters, Org. Biomol. Chem. 1 (2003) 2321.Google Scholar
- [32]K. Smith, S. Almeer, S. J. Black and C. Peters, J. Mat. Chem. 12 (2002) 3285.Google Scholar
- [33]K. Smith, G. A. El-Hiti, M. E. W. Hammond, D. Bahzad, Z. Li and C. Siquet, J. Chem. Soc., Perkin Trans. 1 (2000) 2745.Google Scholar
- [34]K. Smith, G. A. El-Hiti and M. F. Abdel-Megeed, Synthesis (2004) in press.Google Scholar
- [35]K. Smith, G. A. El-Hiti and M. F. Abdel-Megeed, Russ. J. Org. Chem. 39 (2003) 430.Google Scholar
- [36]K. Smith, G. A. El-Hiti and S. A. Mahgoub, Synthesis (2003) 2345.Google Scholar
- [37]K. Smith, G. A. El-Hiti and A. C. Hawes, Synthesis (2003) 2047.Google Scholar
- [38]H. Sasaki, R. Irie, T. Hamada, K. Suzuki and T. Katsuki, Tetrahedron 50 (1994) 11827.Google Scholar
- [39]A. G. Avent, P. A. Chaloner, M. P. Day, K. R. Seddon and T. Welton, J. Chem. Soc., Dalton Trans. (1994) 3405.Google Scholar
- [40]J. D. Holbery and K. R. Seddon, J. Chem. Soc., Dalton Trans. (1999) 2133.Google Scholar
- [41]J. Fuller, R. T. Carlin, H. C. De Long and D. Haworth, J. Chem. Soc., Chem. Commun. (1994) 299.Google Scholar
Copyright information
© Plenum Publishing Corporation 2004