基于（-）-Sparteine的不对称碳锂化反应研究进展
收稿日期: 2013-10-29
修回日期: 2013-11-13
网络出版日期: 2013-11-21
基金资助
国家自然科学基金（No. 21102064）；甘肃省青年科技基金计划（No. 1208RJYA030）；兰州大学中央高校基本业务费（No. lzujbky-2013-73）资助项目.
Progress of Asymmetric Carbolithiation Reactions in the Presence of (-)-Sparteine
Received date: 2013-10-29
Revised date: 2013-11-13
Online published: 2013-11-21
Supported by
Project supported by the National Natural Science Foundation of China (No. 21102064), the Science and Technology Department of Gansu Province (No. 1208RJYA030), and the Fundamental Research Funds for the Central Universities (No. lzujbky-2013-73).
以非活化烯烃为底物，利用（-）-sparteine诱导的分子间-分子内不对称碳锂化反应构建高区域选择性和立体选择性的碳碳新键，合成了一系列手性化合物. 综述了近十几年基于（-）-sparteine的不对称碳锂化反应最新研究成果.
关键词： 非活化烯烃; 分子间-分子内; （-）-sparteine; 对映选择性; 碳锂化反应
田丽霞 , 杜文斌 , 张扬 , 唐寿初 . 基于（-）-Sparteine的不对称碳锂化反应研究进展[J]. 有机化学, 2014 , 34(3) : 507 -514 . DOI: 10.6023/cjoc201310046
Inter-and intra-molecular enantioselective carbolithiation reactions in the presence of (-)-sparteine provide access to construct new highly regio-and stereo-selective carbon-carbon bonds. The recent results of the (-)-sparteine mediated asymmetric carbolithiation reactions in organic synthesis are summarized.
[1] (a) Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 1.
(b) Ma, S.-M.; Xu, B. Chin. J. Org. Chem. 2000, 20, 54 (in Chinese).
(麻生明, 许斌, 有机化学, 2000, 20, 54.;
c) Hogan, A.-M. L.; O'Shea, D. F. Chem. Commun. 2008, 3839.
(d) Gómez-SanJuan, A.; Sotomayor, N.; Lete, E. Beilstein J. Org. Chem. 2013, 9, 313.
[2] Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535.
[3] (a) Xie, X.; Yue, G.; Tang, S.; Huo, X.; Liang, Q.; She, X.; Pan, X. Org. Lett. 2005, 7, 4057.
(b) Tang, S.; Xie, X.; Huo, X.; Liang, Q.; She, X.; Pan, X. Tetrahedron Lett. 2006, 47, 205.
(c) Tang, S.; Han, J.; He, J.; Zheng, J.; He, Y.; Pan, X; She, X. Tetrahedron Lett. 2008, 49, 1348.
[4] Normant, J. F. In Organolithiums in Enantioselective Synthesis, Vol. 5, Ed.: Hodgson, D. M., Springer, Berlin, 2003, p. 287.
[5] Kizirian, J.-C. Chem. Rev. 2008, 108, 140.
[6] Mealy, M. J.; Bailey, W. F. J. Organomet. Chem. 2002, 646, 59.
[7] Fañanás, F. J.; Sanz, R. In The Chemistry of Organolithium Compounds, Vol. 2, Eds.: Rappoport, Z.; Marek, I., Wiley, Chichester, U. K., 2006; p. 295.
[8] Martínez-Estíbalez, U.; Gómez-SanJuan, A.; García-Calvo, O.; Arrasate, S.; Sotomayor, N.; Lete, E. In Targets in Heterocyclic Systems, Vol. 14, Eds.: Attanasi, O.; Spinelli, D., Italian Society of Chemistry, Rome, 2010, p. 124.
[9] Sotomayor, N.; Lete, E. In Science of Synthesis. Knowledge Updates 2011/4, Eds.: Hall, D. G.; Ishikara, K.; Li, J. J.; Marek, I.; North, M.; Schaumann, E.; Weinreb, S. M.; Yus, M., Thieme, Stuttgart, 2011, p. 191.
[10] (a) Couch, J. F. J. Am. Chem. Soc. 1936, 58, 1296.
(b) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282.
[11] Wei, X.; Taylor, R. J. K. Tetrahedron: Asymmetry 1997, 8, 665.
[12] (a) Norsikian, S.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 7523.
(b) Norsikian, S.; Marek, I.; Klein, S.; Poisson, J. F.; Normant, J. F. Chem.-Eur. J. 1999, 5, 2055.
[13] Klein, S.; Marek, I.; Poisson, J.-F.; Normant, J. F. J. Am. Chem. Soc. 1995, 117, 8853.
[14] Dearden, M. J.; McGrath, M. J.; O'Brien, P. J. Org. Chem. 2004, 69, 5789.
[15] Majumdar, S.; de Meijere, A.; Marek, I. Synlett 2002, 423.
[16] (a) Hogan, A.-M. L.; O'Shea, D. F. J. Am. Chem. Soc. 2006, 128, 10360.
(b) Hogan, A.-M. L.; O'Shea, D. F. J. Org. Chem. 2008, 73, 2503.
[17] Peters, J. G.; Seppi, M.; Fröhlich, R.; Wibbeling, B.; Hoppe, D. Synthesis 2002, 381.
[18] Suzuka, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2002, 67, 3355.
[19] Yoshida, J.-I. Chem. Commun. 2005, 4509.
[20] Yoshida, J.-I. Flash Chemistry. Fast Organic Synthesis in Microsystems, Wiley, Chichester, U. K., 2008.
[21] Yoshida, J.-I.; Nagaki, A.; Yamada, T. Chem.-Eur. J. 2008, 14, 7450.
[22] Tomida, Y.; Nagaki, A.; Yoshida, J.-I. Org. Lett. 2009, 11, 3614.
[23] Nieuwland, P. J.; Koch, K.; van Harskamp, N.; Wehrens, R.; van Hest, J. C. M.; Rutjes, F. P. J. T. Chem.-Asian J. 2010, 5, 799.
[24] Tomida, Y.; Nagaki, A.; Yoshida, J.-I. J. Am. Chem. Soc. 2011, 133, 3744.
[25] Tait, M.; Donnard, M.; Minassi, A.; Lefranc, J.; Bechi, B.; Carbone, G.; O'Brien, P.; Clayden, J. Org. Lett. 2013, 15, 34.
[26] Lefranc, J.; Fournier, A. M.; Mingat, G.; Herbert, S.; Marcelli, T.; Clayden, J. J. Am. Chem. Soc. 2012, 134, 7286.
[27] Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K.; Ovaska, T. V.; Rossi, K.; Thiel, Y.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 5720.
[28] Rölle, T.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1995, 1953.
[29] Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanism, Vol. 3, Ed.: Coxon, J. M., JAI Press, Greenwich, 1994, p. 251.
[30] García-Calvo, O.; Sotomayor, N.; Lete, E.; Coldham, I. ARKIVOC 2011, v, 57.
[31] García-Calvo, O.; Coya, E.; Lage, S.; Coldham, I.; Sotomayor, N.; Lete, E. Eur. J. Org. Chem. 2013, 1460
[32] La Cruz, T. E.; Rychnovsky, S. D. J. Org. Chem. 2006, 71, 1068.
[33] Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett 1998, 930.
[34] Pedrosa, R.; Andrés, C.; Iglesias, J. M.; Pérez-Encabo, A. J. Am. Chem. Soc. 2001, 123, 1817.
[35] Coldham, I.; Price, K. N.; Rathmell, R. E. Org. Biomol. Chem. 2003, 1, 2111.
[36] Hoppe, D.; Hintze, F.; Tebben, P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1422.
[37] Woltering, M. J.; Frölich, R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1764.
[38] Hoppe, D.; Woltering, M. J.; Oestrich, M.; Frölich, R. Helv. Chim. Acta 1999, 82, 1860.
[39] Woltering, M. J.; Fröhlich, R.; Wibbeling, B.; Hoppe, D. Synlett 1998, 797.
[40] Bailey, W. F.; Mealy, M. J. J. Am. Chem. Soc. 2000, 122, 6787.
[41] Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789.
[42] Mealy, M. J.; Luderer, M. R.; Bailey, W. F.; Sommer, M. B. J. Org. Chem. 2004, 69, 6042.
[43] O'Brien, P. Chem. Commun. 2008, 655.
[44] Barluenga, J.; Fañanás, F. J.; Sanz, R.; Marcos, C. Org. Lett. 2002, 4, 2225.
[45] Groth, U.; Koettgen, P.; Langenbach, P.; Lindenmaier, A.; Schütz, T.; Wiegand, M. Synlett 2008, 1301.
[46] Martínez-Estíbalez, U.; Sotomayor, N.; Lete, E. Org. Lett. 2009, 11, 1237.
/
| 〈 |
|
〉 |
