Chinese Journal of Organic Chemistry >
Bisperfluorobutylsulfonate Bisbutyltin Catalyzed Allylation and Mukaiyama-aldol Reaction of Aldehyde
Received date: 2012-09-22
Revised date: 2012-10-21
Online published: 2012-11-02
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21172061, 21273068).
Bisperfluorobutylsulfonate bisbutyltin complex was successfully synthesized by treating C4F9SO3Ag with Bu2SnCl2 in acetone at room temperature. When the complex was exposed to air two days, 1H NMR spectra showed that its structure had no change. TG-DSC showed that the complex was stable below 220 ℃. The complex had a good solubility in polar solvents, such as ethyl acetate, acetone, acetonitrile, THF, ethyl ether. But it was poor soluble in hexane, CH2Cl2, toluene at room temperature. In the presence of 1.0 and 5.0 mol% of bisperfluorobutylsulfonate bisbutyltin respectively, allylation of aldehyde and Mukaiyama aldol reaction could efficiently occur in CH3CN at room temperature and give high yield of the corresponding products.
Liu Yi , Wang Xie , Chen Jinyang , Li Ningbo , Xu Xinhua . Bisperfluorobutylsulfonate Bisbutyltin Catalyzed Allylation and Mukaiyama-aldol Reaction of Aldehyde[J]. Chinese Journal of Organic Chemistry, 2012 , 32(12) : 2328 -2333 . DOI: 10.6023/cjoc201209032
[1] Mannix, L. K.; Files, J. A. CNS Drugs 2005, 19, 951.
(b) Goadsby, P. J. Nat. Rev. Drug Discovery 2005, 4, 741.
(c) Buchanan, T. M.; Ramadan, N. M.; Aurora, S. Exp. Rev. Neurother. 2004, 4, 391.
[2] (a) Trofimov, B. A.; Nedolya, N. A. In Comprehensive Heterocyclic Chemistry III, Vol. 3, Eds.: Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K.; Jones, G.; Elsevier, Oxford, 2008, pp. 110～133.
(b) Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608.
(c) Rosa, M. D.; Soriente, A. Eur. J. Org. Chem. 2010, 1029.
(d) Desroses, M.; Wieckowski, K.; Stevens, M.; Odell, L. R. Tetrahedron Lett. 2011, 52, 4417.
(e) Ballini, R.; Palmieri, A.; Petrini, M.; Torregiani, E. Org. Lett. 2006, 8, 4093.
[3] (a) Trsushimoto, T.; Kanbara, M. Org. Lett. 2011, 13, 912.
(b) Rizzo, J. R.; Alt, C. A.; Zhang, T. Y. Tetrahedron Lett. 2008, 49, 6749.
(c) Imm, S.; Bähn, S.; Tillack, A.; Mevius, K.; Nenbert, L.; Beller, M. Chem. Eur. J. 2010, 16, 2705.
[4] (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
(b) Ojima, I. Catalytic Asymmetric Synthesis, Wiley-VCH, New York, 2000.
(c) Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organimetallic Compounds, 2nd ed., Wiley-VCH, Weinheim, 2002.
(d) Woodmansee, D. H.; Pfaltz, A. In Topics in Organometallic Chemistry, Springer-Verlag BerlinHeidelberg, 2011, pp. 31～76.
[5] (a) Cui, X.; Burgess, K. Chem. Rev. 2005, 105, 3272.
(b) Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402.
(c) Perry, M. C.; Cui, X.; Powell, M. T.; Hou, D. R.; Reibenspies, J. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 113.
(d) Cui, X.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14212.
(e) Zhao, J.; Burgess, K. J. Am. Chem. Soc. 2009, 131, 13236.
(f) Mazuela, J.; Norrby, P.-O.; Andersson, P. G.; Pàmies, O.; Diéguez, M. J. Am. Chem. Soc. 2011, 133, 13634.
[6] (a) Pelmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
(b) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis, Vol. III, Springer, New York, 1999, pp. 1105～1143.
(c) Berner, M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
(d) Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933.
(e) Sulzer-Mossé, S.; Alexakis, A. Chem. Commun. 2007, 3123.
(f) Jautze, S.; Peters, R. Synthesis 2010, 365.
[7] Selected recent reviews about asymmetric conjugate additions:
(a) Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279.
(b) Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796.
(c) Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824.
(d) Jautze, S.; Peters, R. Synthesis 2010, 365.
[8] (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
(b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
(c) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221.
(d) Li, K.; Alexakis, A. Tetrahedron Lett. 2005, 46, 8019.
(e) Li, K.; Alexakis, A. Tetrahedron Lett. 2005, 46, 5823.
(f) Isleyen, A.; Dogan, ö. Tetrahedron: Asymmetry 2007, 18, 679.
(g) Escorihuela, J.; Burguete, M. I.; Luis, S. V. Tetrahedron Lett. 2008, 49, 6885.
(h) Dong, Z.-B.; Liu, B.; Fang, C.; Li, J.-S. J. Organomet. Chem. 2008, 693, 17.
(i) Kawamura, K.; Fukukawa, H.; Hayashi, M. Org. Lett. 2008, 10, 3509.
(j) Xie, Y.; Huang, H.; Mo, W.; Fan, X.; Shen, Z.; Shen, Z.; Sun, N.; Hu, B.; Hu, X. Tetrahedron: Asymmetry 2009, 20, 1425.
(k) Endo, K.; Ogawa, M.; Shibata, T. Angew. Chem., Int. Ed. 2010, 49, 2410.
(l) Tauchman, J.; Císa?ová, I.; Štěpni?ka, P. Eur. J. Org. Chem. 2010, 4276.
(m) Zhao, Q.-L.; Tse, M. K.; Wang, L. L.; Xing, A.-P.; Jiang, X. Tetrahedron: Asymmetry 2010, 21, 2788.
(n) Rachwalski, M.; Le?niak, S.; Kie?basiński, P. Tetrahedron Asymmetry 2010, 21, 1890.
(o) MikláŠová, N. N.; Julínek, O.; MeŠková, M.; Setni?ka, V.; Urbanová, M. Tetrahderon Lett. 2010, 51, 1966.
(p) Ni, C.-Y.; Kan, S.-S.; Liu, Q.-Z.; Kang, T.-R. Org. Biomol. Chem. 2011, 9, 6211.
[9] Palmieri, A.; Petrini, M.; Shaikh, R. R. Org. Biomol. Chem. 2010, 8, 1259.
[10] Jing, L.; Wei, J.; Zhou. L.; Huang, Z.; Li, Z.; Wu, D.; Xiang, H.; Zhou, X. Chem. Eur. J. 2010, 16,10955.
[11] Shaikh, R. R.; Mazzanti, A.; Petrini, M.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8707.
[12] Zheng, B.-H.; Ding, C.-H.; Hou, X.-L; Dai, L.-X. Org. Lett. 2010, 12, 1688.
[13] (a) Dobish, M. C.; Johnston, J. N. Org. Lett. 2010, 12, 5744.
(b) Ballini, R.; Palmieri, A.; Petrini, M.; Shaikh, R. R. Adv. Synth. Catal. 2008, 350, 129.
[14] Palmieri, A.; Petrini, M. J. Org. Chem. 2007, 72, 1863.
[15] Marcili, L.; Palmieri, A.; Petrini, M. Org. Biomol. Chem. 2010, 8, 706.
[16] Jagt, R. B. C.; Toullec, P. Y.; Schudde, E. P.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. J. Comb. Chem. 2007, 9, 407.
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