Phosphine-catalyzed [4+2] annulations of α-aminonitriles with allenoates: Synthesis of functionalized tetrahydropyridines

Abstract

Phosphine-catalyzed [4+2] annulations of 2-(acetoxymethyl)buta-2,3-dienoates with α-aminonitriles have been developed, in which α-aminonitriles serve as C, N-bisnucleophilic reaction partners and 2-(acetoxymethyl)buta-2,3-dienoates as “C4 synthons” respectively. A number of α-aminonitriles could be successfully applied to giving multifunctional desired products using PPh₃ as catalyst. This method provides a facile entry to access polysubstituted tetrahydropyridines bearing quaternary carbon centers. The possible reaction mechanism was also proposed.

Keywords

Annulation / Catalysis / Tetrahydropyridine

References

[1] Benito A., Pedro A., Cristina A. Curr. Opin. Drug Discovery Dev., 2010, 13(6): 685.

[2] Wimone R., Currie K. S., Mitchell S. A., Darrow J. W., Pippin D. A. Comb Chem. High Throughput Screen, 2004, 7: 473.

[3] Leeson P. D., Springthorpe B. Nat. Rev. Drug. Discov., 2007, 6: 881.

[4] Daly J. W., Spande T. F., Garraffo H. M. J. Nat. Prod., 2005, 68(10): 1556.

[5] Michael J. P. Nat. Prod. Rep., 2008, 25: 139.

[6] Michael J. P. The Alkaloids, 2001, San Diego: Academic Press, 55.

[7] Comins D. L., Joseph S. P. Advances in Nitrogen Heterocycles, 1996, Greenwich, CT: JAI. Press, 251.

[8] Rowland G. B., Rowland E. B., Zhang Q., Antilla J. C. Curr. Org. Chem., 2006, 10(9): 981.

[9] Kouznetsov V. V. Tetrahedron, 2009, 65: 2721.

[10] Girling P. R., Kiyoi T., Whiting A. Org. Biomol. Chem., 2011, 9: 3105.

[11] Memeo M. G., Quadrelli P. Chem. Eur. J., 2012, 18(40): 12554.

[12] Masson G., Lalli C., Benohoud M., Dagousset G. Chem. Soc. Rev., 2013, 42: 902.

[13] Lu X., Zhang C., Xu Z. Acc. Chem. Res., 2001, 34: 535.

[14] Methot J. L., Roush W. R. Adv. Synth. Catal., 2004, 346: 1035.

[15] Lu X., Du Y., Lu C. Pure Appl. Chem., 2005, 77: 1985.

[16] Cowen B. J., Miller S. J. Chem. Soc. Rev., 2009, 38: 3102.

[17] Ye L. W., Zhou J., Tang Y. Chem. Soc. Rev., 2008, 37: 1140.

[18] Denmark S. E., Beutner G. L. Angew. Chem. Int. Ed., 2008, 47: 1560.

[19] Wei Y., Shi M. Acc. Chem. Res., 2010, 43: 1005.

[20] Zhao Q. Y., Lian Z., Wei Y., Shi M. Chem. Commun., 2012, 48: 1724.

[21] Wang Z., Xu X., Kwon O. Chem. Soc. Rev., 2014, 43: 2927.

[22] Xu Z., Lu X. Tetrahedron. Lett., 1997, 38(19): 3461.

[23] Xu Z., Lu X. J. Org. Chem., 1998, 63: 5031.

[24] Zhu X. F., Lan J., Kwon O. J. Am. Chem. Soc., 2003, 125: 4716.

[25] Guo H., Xu Q., Kwon O. J. Am. Chem. Soc., 2009, 131: 6318.

[26] Chen X. Y., Ye S. Eur. J. Org. Chem., 2012, 5723.

[27] Wurz R. P., Fu G. C. J. Am. Chem. Soc., 2005, 127: 12234.

[28] Xiao H., Chai Z., Wang H. F., Wang X. W., Cao D. D., Liu W., Lu Y. P., Yang Y. Q., Zhao G. Chem. Eur. J., 2011, 17: 10562.

[29] Zhang Q., Yang L., Tong X. J. Am. Chem. Soc., 2010, 132: 2550.

[30] Hu P., Hu J., Jiao J., Tong X. Angew. Chem. Int. Ed., 2013, 52: 5319.

[31] Albright J. D. Tetrahedron, 1983, 39: 3207.

[32] Enders D., Shilvock J. P. Chem. Soc. Rev., 2000, 29: 359.

[33] Opatz T. Synthesis, 2009, 12: 1941.

[34] Meyer N., Werner F., Opatz T. Synthesis, 2005, 6: 945.

[35] Bergner I., Opatz T. Synthesis, 2007, 6: 918.

[36] Pan F., Chen J. M., Zhuang Z., Fang Y. Z., Zhang S. X. A., Liao W. W. Org. Biomol. Chem., 2012, 10: 2214.

[37] Pan F., Chen J. M., Qin T. Y., Zhang S. X. A., Liao W. W. Eur. J. Org. Chem., 2012, 5324.

[38] En D., Zou G. F., Guo Y., Liao W. W. J. Org. Chem., 2014, 79: 4456.

[39] Zhuang Z., Pan F., Fu J. G., Chen J. M., Liao W. W. Org. Lett., 2011, 13: 6164.

[40] Chen J. M., Fang Y. Z., Wei Z. L., Liao W. W. Synthesis, 2012, 44: 1849.

[41] Qin T. Y., Liao W. W., Zhang Y. J., Zhang S. X. A. Org. Biomol. Chem., 2013, 11: 984.

[42] Chen J. M., Zou G. F., Liao W. W. Angew. Chem. Int. Ed., 2013, 52: 9296.