Organocatalyzed cascade reactions of cyclic β-enamino esters and α,β-unsaturated aldehydes leading to indoloquinolizidines and benzoquinolizidines

European Journal of Organic Chemistry

Volumn , Issue 33, 2011, Pages 6755-6763

  Wu, Xiaoyu ^a   Nie, Linlin ^a   Fang, Huihui ^a   Chen, Jie ^a   Cao, Weiguo ^a   Zhao, Gang ^b  

^a SHANGHAI UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

Conjugate addition; Cyclization; Domino reactions; Nitrogen heterocycles; Organocatalysis

Indexed keywords

EID: 80855144782     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201101105     Document Type: Article

References (57)

1. For selected reviews on organocatalysis, see: Acc. Chem. Res. 2004, 37 (8), special issue on organocatalysis
2. A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, Germany, 2004.
3. Chem. Rev. 2007, 107 (12), special issue on organocatalysis.
4. P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007.
5. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232;
6. Angew. Chem. Int. Ed. 2008, 47, 6138.
7. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178.
8. R. Matsubara, S. Kobayashi, Acc. Chem. Res. 2008, 41, 292 and reference cited therein.
9. Other examples of Lewis-acid-catalyzed reactions employing enamides as nucleophiles:, L. Yang, D. X. Wang, Z. T. Huang, M. X. Wang, J. Am. Chem. Soc. 2009, 131, 10390.
10. L. Yang, C. H. Lei, D. X. Wang, Z. T. Huang, M. X. Wang, Org. Lett. 2010, 12, 3918.
11. L. Chang, Y. L. Kuang, B. Qin, X. Zhou, X. H. Liu, L. L. Lin, X. M. Feng, Org. Lett. 2010, 12, 2214.
12. M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2006, 118, 2312;
13. Angew. Chem. Int. Ed. 2006, 45, 2254.
14. M. Terada, K. Machioka, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 10336.
15. Q. X. Guo, Y. G. Peng, J. W. Zhang, L. Song, Z. Feng, L. Z. Gong, Org. Lett. 2009, 11, 4620.
16. H. Liu, G. Dagousset, G. Masson, P. Retailleau, J. Zhu, J. Am. Chem. Soc. 2009, 131, 4598.
17. M. Lu, Y. P. Lu, D. Zhu, X. F. Zeng, X. S. Li, G. F. Zhong, Angew. Chem. 2010, 122, 8770;
18. Angew. Chem. Int. Ed. 2010, 49, 8588.
19. L. S. Zu, H. X. Xie, H. Li, J. Wang, X. H. Yu, W. Wang, Chem. Eur. J. 2008, 14, 6333.
20. Y. Hayashi, H. Gotoh, R. Masui, H. Ishikawa, Angew. Chem. 2008, 120, 4076;
21. Angew. Chem. Int. Ed. 2008, 47, 4012.
22. K. Yoshida, T. Inokuma, K. Takasu, Y. Takemoto, Synlett 2010, 1865.
23. K. Yoshida, T. Inokuma, K. Takasu, Y. Takemoto, Molecules 2010, 15, 8305.
24. A. Noole, M. Borissova, M. Lopp, T. Kanger, J. Org. Chem. 2011, 76, 1538.
25. K. Paulvannan, J. R. Stille, Tetrahedron Lett. 1993, 34, 6673.
26. K. Paulvannan, J. B. Schwarz, J. R. Stille, Tetrahedron Lett. 1993, 34, 215.
27. G. R. Cook, L. G. Beholz, J. R. Stille, J. Org. Chem. 1994, 59, 3575.
28. N. S. Barta, B. Brode, J. R. Stille, J. Am. Chem. Soc. 1994, 116, 6201.
29. K. Paulvannan, J. R. Stille, J. Org. Chem. 1994, 59, 1613.
30. P. Benovsky, J. R. Stille, Tetrahedron Lett. 1997, 38, 8475.
31. Y. Cheng, Z. T. Huang, M. X. Wang, Curr. Org. Chem. 2004, 8, 325.
32. N. Sydorenko, R. P. Hsung, O. S. Darwish, J. M. Hahn, J. Liu, J. Org. Chem. 2004, 69, 6732.
33. A. I. Gerasyuto, R. P. Hsung, Org. Lett. 2006, 8, 4899.
34. A. I. Gerasyuto, R. P. Hsung, J. Org. Chem. 2007, 72, 2476.
35. X. Y. Wu, X. Y. Dai, L. L. Nie, H. H. Fang, J. Chen, Z. J. Ren, W. G. Cao, G. Zhao, Chem. Commun. 2010, 46, 2733.
36. H. H. Fang, X. Y. Wu, L. L. Nie, X. Y. Dai, J. Chen, W. G. Cao, G. Zhao, Org. Lett. 2010, 12, 5366.
37. X. Y. Dai, X. Y. Wu, H. H. Fang, L. L. Nie, J. Chen, H. M. Deng, W. G. Cao, G. Zhao, Tetrahedron 2011, 67, 3034.
38. For examples of conjugate additions promoted by prolinol TMS ether, see: S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411;
39. Angew. Chem. Int. Ed. 2006, 45, 4305.
40. A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119;
41. Angew. Chem. Int. Ed. 2007, 46, 1101.
42. A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jørgensen, Chem. Commun. 2006, 4928.
43. The cyclic enamino esters 1 were prepared according to a literature procedure:, L. F. Tietze, Y. Zhou, E. Töpken, Eur. J. Org. Chem. 2000, 2247.
44. When we were preparing the manusript, Hsung and co-workers developed a cyclization reaction between pyrrolidine-based exocyclic vinylogous amides and urethanes with α,β-unsaturated aldehydes to afford substituted indolizidines with up to 70 % ee:, G. S. Buchanan, H. Dai, R. P. Hsung, A. I. Gerasyuto, C. M. Scheinebeck, Org. Lett. 2011, 13, 4402.
45. For examples of domino reactions involving formation of hemi-aminoacetals, see: R. Rios, I. Ibrahem, J. Vesely, H. Sundén, A. Cõrdova, Tetrahedron Lett. 2007, 48, 8695.
46. G. Valero, J. Schimer, I. Cisarova, J. Vesely, A. Moyano, R. Rios, Tetrahedron Lett. 2009, 50, 1943.
47. J. Franzén, A. Fisher, Angew. Chem. 2009, 121, 801;
48. Angew. Chem. Int. Ed. 2009, 48, 787.
49. The Alkaloids: Chemistry and Biology, vol. 50 (Ed.:, G. A. Cordell), Academic Press, New York, 1998.
50. C. Szántay, K. Honty, in The Chemistry of Heterocyclic Compounds, vol. 25 (Ed.:, J. E. Saxton), Wiley, New York, 1994, pp. 161-216.
51. E. W. Baxter, P. S. Marino, in Alkaloids: Chemical and Biological Perspectives, vol. 8 (Ed.:, S. W. Pelletier), Springer-Verlag, New York, 1992, pp. 197-319.
52. J. A. Marshall, W. S. Johnson, J. Org. Chem. 1963, 28, 421.
53. W. S. Johnson, V. J. Bauer, R. W. Franck, Tetrahedron Lett. 1961, 2, 72.
54. J. A. Marshall, W. S. Johnson, J. Am. Chem. Soc. 1962, 84, 1485.
55. H. Takayamaa, R. Yamamotoa, M. Kurihara, M. Kitajima, N. Aimi, L. Mao, S. Sakai, Tetrahedron Lett. 1994, 35, 8813.
56. Y. Torisawa, A. Hashimoto, M. Nakagawa, T. Hino, Tetrahedron Lett. 1989, 30, 6549.
57. P. Benovsky, J. R. Stille, Tetrahedron Lett. 1997, 38, 8475.