Abstract
Ionic-liquid-supported proline derivative was synthesized starting from L-proline and was used to catalyze direct asymmetric aldol reaction of acetone with aldehydes. The yield and optical purity of the condensation products, the corresponding β-hydroxy carbonyl compounds were comparable with those obtained under homogeneous conditions. Moreover, the catalyst can be reused for at least four times.
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References
Comprehensive Organic Synthesis, Trost, B.M. and Fleming, I., Eds., Oxford: Pergamon, 1991, vol. 2; Palomo, C., Oiarbide, M., and Garcia, J.M., Chem. Eur. J., 2002, vol. 8, p. 36.
Trost, B.M., Science, 1991, vol. 254, p. 1471; Trost, B.M., Angew. Chem., Int. Ed. Engl., 1995, vol. 34, p. 259.
List, B., Lerner, R.A., and Barbas, C.F., III, J. Am. Chem. Soc., 2000, vol. 122, p. 2395; Trost, B.M. and Ito, H., J. Am. Chem. Soc., 2000, vol. 122, p. 12 003.
Sakthivel, K., Notz, W., Bui, T., and Barbas, C.F., III, J. Am. Chem. Soc., 2001, vol. 123, p. 5260.
List, B. and Castello, C., Org. Lett., 2001, vol. 3, p. 573; Trost, B.M., Ito, H., and Silcoff, E., J. Am. Chem. Soc., 2001, vol. 123, p. 3367; List, B., Tetrahedron, 2002, vol. 58, p. 5573; Burgevig, A., Poulsen, T.B., Zhuang, W., and Jørgensen, K.A., Synlett, 2003, p. 1915; Pan, Q., Zou, B., Wang, Y., and Ma, D., Org. Lett., 2004, vol. 6, p. 1009.
Welton, T., Chem. Rev., 1999, vol. 99, p. 2071; Wasserscheid, P. and Keim, W., Angew. Chem., Int. Ed., 2000, vol. 39, p. 3772; Wilkes, J.S., Green Chem., 2002, vol. 4, p. 73; Ionic Liquids in Synthesis, Wasserscheid, P. and Welton, T., Eds., Weinheim: Wiley, 2003.
Fuller, J., Carlin, R.T., and Osteryoung, R.A., J. Electrochem. Soc., 1997, vol. 144, p. 3881.
Huddleston, J.G., Willauer, H., Swatloski, R.P., Visser, A.E., and Rogers, R.D., Chem. Commun., 2001, p. 1765; Bosmann, A., Datsevich, L., Jess, A., Lauter, A., Schmitz, C., and Wasserscheid, P., Chem. Commun., 2001, p. 2494.
Ye, C., Liu, W., Chen, Y., and Yu, L., Chem. Commun., 2001, p. 2244.
Kimizuka, N. and Nakashima, T., Langmuir, 2001, vol. 17, p. 6759; Leone, A.M., Weatherly, S.C., Williams, M.K., Thorp, H.H., and Murray, R.W., J. Am. Chem. Soc., 2001, vol. 123, p. 218.
Fraga-Dubreuil, J., Bazureau, J., and Bazureau, J.P., Tetrahedron Lett., 2001, vol. 42, p. 6097; Fraga-Dubreuil, J. and Bazureau, J.P., Tetrahedron, 2003, vol. 59, p. 6121.
Loh, T.-P., Feng, L.-C., Yang, H.Y., and Yang, J.-Y., Tetrahedron Lett., 2002, vol. 43, p. 8741.
Peter, K., Iveta, K., Battsengel, G., and Stefan, T., Chem. Commun., 2002, p. 2510; Michelangelo, G., Serena, R., Paolo, L.M., Francesca, D.A., and Renato, N., Tetrahedron Lett., 2004, vol. 45, p. 6113.
Miao, W. and Chan, T.-H., J. Org. Chem., 2005, vol. 70, p. 3251.
Tang, Z., Jiang, F., Yu, L.-T., Gong, L.-Z., Mi, A.-Q., Jiang, Y.-Z., and Wu, Y.-D., J. Am. Chem. Soc., 2003, vol. 125, p. 5262.
Branco, L.C., Rosa, J.N., Moura Ramos, J.J., and Afonso, C.A.M., Chem. Eur. J., 2002, vol. 8, p. 3671.
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Published in Russian in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 12, pp. 1834–1837.
The text was submitted by the authors in English.
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Chen, Z., Li, Y., Xie, H. et al. Ionic liquid-supported proline as catalyst in direct asymmetric aldol reaction. Russ J Org Chem 44, 1807–1810 (2008). https://doi.org/10.1134/S1070428008120154
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DOI: https://doi.org/10.1134/S1070428008120154