OALib Journal期刊
不对称有机催化Michael加成/半缩醛胺化/酰亚胺正离子环化串联反应研究进展有机化学
DOI: 10.6023/cjoc201208032
Keywords: 有机催化 ,串联反应 ,氮杂多环 ,生物碱
Abstract:
随着近十多年来不对称有机小分子催化的发展,以这类催化为基础的串联反应也取得了很大的进展.综述了近几年来不对称有机催化Michael加成/半缩醛胺化/酰亚胺正离子环化串联反应构建手性氮杂多环结构的研究进展,介绍了国内外多个课题组对这一类反应的研究结果以及该类反应在生物碱合成中的应用.
References
[1] For reviews, see: (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. [2] (c) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. [3] (e) Yet, L. Chem. Rev. 2000, 100, 2963. [4] (g) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127. [5] (h) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395. [6] (j) Jakopin, Z.; Dolenc, M. S. Curr. Med. Chem. 2010, 17, 651. [7] (b) Liddell, J. R. Nat. Prod. Rep. 2002, 19, 773. [8] (d) O’Hagan, D. Nat. Prod. Rep. 2000, 17, 435. [9] (f) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862. [10] (b) List, B.; Yang, J.-W. Science 2006, 313, 1584. [11] (d) Marigo, M.; J？rgensen, K. A. Chem. Commun. 2006, 2001. [12] (f) Dalko, P. I. Enantioselective Organocatalysis: Reactions and Experimental Procedures, Wiley-VCH, Weinheim, 2007. [13] (h) Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138. [14] (i) Bertelsen, S.; J？rgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178. [15] (b) Grondal, C.; Matthieu, J.; Enders, D. Nat. Chem. 2010, 2, 167. [16] (d) Bernhard, W.; Muhammad, A.; Sander, S. B. Angew. Chem., Int. Ed. 2010, 49, 846. [17] (f) Pellissier, H. Adv. Synth. Catal. 2012, 354, 237. [18] Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030. [19] (b) Carlone, A.; Cabrera, S.; Marigo, M.; J？rgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1101. [20] For reviews on organocatalytic conjugate additions, see: (a) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701. [21] (c) Zhu, Q.; Lu, Y. X. Aust. J. Chem. 2009, 62, 951. [22] (e) Sulzer-Mosse, S.; Alexakis, A. Chem. Commun. 2007, 3123. [23] St？ckigt, J.; Antonchick, A. P.; Wu, F. R.; Waldmann, H. Angew. Chem., Int. Ed. 2011, 50, 8538. [24] (b) Zhang, W.; Franzen, J. Adv. Synth. Catal. 2010, 352, 499. [25] (a) Cordell, G. A. The Alkaloids: Chemistry and Biology, Vol. 50, Academic Press, New York, 1998. [26] (c) Baxter E. W.; Mariano, P. S. In Alkaloids: Chemical and Biological Perspectives, Vol. 8, Ed.: Pelletier, S. W., Springer, New York, 1992, p. 197. [27] (a) Wu, X. Y.; Dai, X. Y.; Nie, L. L.; Fang, H. H.; Chen, J.; Ren, Z. J.; Cao, W. G.; Zhao, G. Chem. Commun. 2010, 46, 2733. [28] (c) Dai, X. Y.; Wu, X. Y.; Fang, H. H.; Nie, L. L.; Chen, J.; Deng, H. M.; Cao, W. G.; Zhao, G. Tetrahedron 2011, 67, 3034. [29] (e) Wu, X. Y.; Fang, H. H.; Liu, Q.; Nie, L. L.; Chen, J.; Cao, W. G.; Zhao, G. Tetrahedron 2011, 67, 7251. [30] Deiters, A.; Chen, K.; Eary, C. T.; Martin, S. F. J. Am. Chem. Soc. 2003, 125, 4541. [31] Rueping, M.; Volla, C. M. R. RSC Adv. 2011, 1, 79. [32] (b) Akiyama, T.; Itoh J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999. [33] (d) Doyle A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713. [34] (e) Kampen, D.; Reisinger C. M.; List, B. Top. Curr. Chem. 2010, 291, 395. [35] Lin, S. Z.; Deiana, L.; Tseggai, A.; Córdova, A. Eur. J. Org. Chem. 2012, 398. [36] Rueping, A. M.; Volla, C. M. R.; Bolte, M.; Raabe, G. Adv. Synth. Catal. 2011, 353, 2853. [37] Hirst, G. C. In Encyclopedia of Reagents for Organic Synthesis, Vol. 5, Ed.: Paquette, L. A., Wiley, New York, 1995, p. 3576. [38] (b) Tejedor, D.; López-Tosco, S.; Fabio Cruz-Acosta, F.; Méndez-Abt, G.; García-Tellado, F. Angew. Chem., Int. Ed. 2009, 48, 2090. [39] (b) Tejedor, D.; Santos-Expósito, A.; García-Tellado, F. Chem. Eur. J. 2007, 13, 1201. [40] (b) Lin, L.; Jiang, X.; Liu, W.; Qiu, L.; Xu, Z.; Xu, J.; Chan, A. S. C.; Wang, R. Org. Lett. 2007, 9, 2329. [41] (d) Fujimori, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 4964. [42] (c) Marshall, J. A.; Johnson, W. S. J. Am. Chem. Soc. 1962, 84, 1485. [43] (b) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079. [44] (d) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285. [45] (f) Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845. [46] (h) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395. [47] Jin, Z. C.; Huang, H. C.; Li, W. J.; Luo, X. Y.; Liang, X. M.; Ye, J. X. Adv. Synth. Catal. 2011, 353, 343. [48] Jin, Z. C.; Wang, X.; Huang, H. C.; Liang, X. M.; Ye, J. X. Org. Lett. 2011, 13, 564. [49] Zhou, S. L.; Li, J. L.; Dong, L.; Chen, Y. C. Org. Lett. 2011, 13, 5874. [50] (b) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079. [51] (d) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285. [52] (f) Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845. [53] (i) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. [54] For selected references: (a) Enders, D.; Thiebes, T. Pure Appl. Chem. 2001, 73, 573. [55] (c) Michael, J. P. Nat. Prod. Rep. 2001, 18, 520. [56] (e) Saxton, J. E. Nat. Prod. Rep. 1997, 14, 559. [57] For selected reviews on organocatalysis, see: (a) Berkessel, A.; Groger, H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2004. [58] (c) List, B. Chem. Commun. 2006, 819. [59] (e) Special issue on organocatalysis: Chem. Rev. 2007, 107, 5413. [60] (g) Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638. [61] For selected reviews, see: (a) Yu, X. H.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037. [62] (c) Alba, A. N.; Companyó, X.; Viciano, M.; Rios, R. Curr. Org. Chem. 2009, 13, 1432. [63] (e) Peng, F. Z.; Shao, Z. H. Curr. Org. Chem. 2011, 15, 4144. [64] Royer, J.; Bonin, M.; Micoui, L. Chem. Rev. 2004, 104, 2311 and references therein. [65] For examples of conjugate additions promoted by prolinol TMS ether, see: (a) Brandau, S.; Landa, A.; Franzén, J.; Marigo, M.; J？rgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 4305. [66] (c) Carlone, A.; Marigo, M.; North, C.; Landa, A.; J？rgensen, K. A. Chem. Commun. 2006, 4928. [67] (b) Enders, D.; Wang, C.; Liebich, J. X. Chem. Eur. J. 2009, 15, 11058. [68] (d) Vicario, J. L.; Badia, D.; Carrillo, L. Synthesis 2007, 2065. [69] (f) Ying, A. G.; Wu, C. L.; Fu, Y. Q.; Ren, S. B.; Liang, H. D. Chin. J. Org. Chem. 2012, 32, 1587 (in Chinese). (应安国, 武承林, 付永前, 任世斌, 梁华定, 有机化学, 2012, 32, 1587.) [70] (a) Franzén, J.; Fisher, A. Angew. Chem., Int. Ed. 2009, 48, 787. [71] (b) Szántay C.; Honty, K. The Chemistry of Heterocyclic Compounds, Vol. 25, Ed.: Saxton, J. E., Wiley, New York, 1994, p. 161. [72] (b) Fang, H. H.; Wu, X. Y.; Nie, L. L.; Dai, X. Y.; Chen, J.; Cao, W. G.; Zhao, G. Org. Lett. 2010, 12, 5366. [73] (d) Wu, X. Y.; Zhang, Y.; Dai, X. Y.; Fang, H. H.; Chen, J.; Cao, W. G.; Zhao, G. Synthesis 2011, 3675. [74] (f) Wu, X. Y.; Dai, X. Y.; Fang, H. H.; Nie, L. L.; Chen, J.; Cao, W. G.; Zhao, G. Chem. Eur. J. 2011, 17, 10510. [75] Zhang, W.; Bah, J.; Wohlfarth, A.; Franzén, J. Chem. Eur. J. 2011, 17, 13814. [76] Reviews on chiral Br？nsted acid catalysis: (a) Bolm, C.; Rantanen, T.; Schiffers I.; Zani, L. Angew. Chem., Int. Ed. 2005, 44, 1758. [77] (c) Akiyama, T. Chem. Rev. 2007, 107, 5744. [78] (f) Yamamoto H.; Payette, N. In Hydrogen Bonding in Organic Synthesis, Ed.: Pihko P. M., Wiley-VCH, Weinheim, 2009, p. 73. [79] Franke, P. T.; Richter, B.; J？rgensen, K. A. Chem. Eur. J. 2008, 14, 6317. [80] (a) Tejedor, D.; González-Cruz, D.; Santos-Expósito, A.; Marrero- Tellado, J. J.; de Armas, P.; García-Tellado, F. Chem. Eur. J. 2005, 11, 3502. [81] For selected examples of domino reactions and MCRs employing alkyl propiolates as reaction partners, see: (a) Tejedor, D.; Santos-Expósito, A.; García-Tellado, F. Chem. Commun. 2006, 2667. [82] For selected examples of asymmetric catalyzed addition of alkyl propiolates to electrophiles, see: (a) Gao, G.; Wang, Q.; Yu, X. Q.; Xie, R. G.; Pu, L. Angew. Chem., Int. Ed. 2005, 45, 122. [83] (c) Trost, B. M.; Weiss, A. H.; Jacobi von Wangelin, A. J. Am. Chem. Soc. 2006, 128, 8. [84] (a) Marshall, J. A.; Johnson, W. S. J. Org. Chem. 1963, 28, 421. [85] (b) Johnson, W. S.; Bauer, V. J.; Franck, R. W. Tetrahedron Lett. 1961, 2, 72. [86] (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. [87] (c) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. [88] (e) Yet, L. Chem. Rev. 2000, 100, 2963. [89] (g) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127. [90] (i) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. [91] Jin, Z. C.; Yu, F.; Wang, X.; Huang, H. C.; Luo, X. Y.; Liang, X. M.; Ye, J. X. Org. Biomol. Chem. 2011, 9, 1809. [92] Jiang, J.; Qing, J.; Gong, L. Z. Chem. Eur. J. 2011, 15, 7031. [93] Zhu, H. L.; Ling, J. B.; Xu, P. F. J. Org. Chem. 2012, 77, 7737.
Full-Text
Contact Us
service@oalib.com
QQ:3279437679
WhatsApp +8615387084133
