二乙基锌对原位产生吲哚亚胺的对映选择性加成反应
收稿日期: 2012-07-07
修回日期: 2012-08-02
网络出版日期: 2012-08-06
基金资助
国家自然科学基金(Nos. 21102116, 20772097)资助项目.
Enantioselective Conjugate Addition of Diethylzinc to Vinylogous Imines Generated in situ from Sulfonyl Indoles
Received date: 2012-07-07
Revised date: 2012-08-02
Online published: 2012-08-06
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21102116, 20772097).
倪承燕 , 李文科 , 何龙 , 刘全忠 , 康泰然 . 二乙基锌对原位产生吲哚亚胺的对映选择性加成反应[J]. 有机化学, 2012 , 32(12) : 2322 -2327 . DOI: 10.6023/cjoc201207011
Enantioselective conjugate addition of diethyl zinc to vinylogous imines generated in situ from sulfonyl indoles was developed. Various sulfonyl indoles reacted with diethyl zinc in the presence of chiral phosphoramidites in combination with copper triflate affording the corresponding indole substituted alkanes in up to 99% yield with moderate to good enantioselectivity (up to 80% ee).
[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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