Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives

Chemical Communications

Volumn , Issue 35, 2005, Pages 4481-4483

  Ye, Jinxing ^a   Dixon, Darren J ^a   Hynes, Peter S ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ALKENE DERIVATIVE; ESTER DERIVATIVE; MALONIC ACID DERIVATIVE; NITROSTYRENE; STYRENE DERIVATIVE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; HYDROGEN BOND; MICHAEL ADDITION; SYNTHESIS;

EID: 25444473664     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b508833j     Document Type: Article

References (66)

1. For a review see: (a) O. M. Berner, L. Tedeschi and D. Entiers, Eur. J. Org. Chem. 2002, 1877.
2. Other examples with metal-based catalysts: (b) N. Sewald and V. Wendisch. Tetrahedron: Asymmetry. 1998, 9, 1341.
3. (c) C. A. Luchaco-Cullis and A. H. Hoveyda, J. Am. Chem. Soc. 2002. 124, 8192.
4. (d) A. Duursma, A. J. Minnaard and B. L. Feringa, J. Am. Chem. Soc. 2003, 125, 3700.
5. (e) H. Choi, Z. M. Hua and I. Ojima, Org. Lett., 2004, 6, 2689.
6. (a) D. M. Barnes, J. G. Ji, M. G. Fickes, M A. Fitzgerald, S. A. King, H. E. Mortem, F. A. Plagge, M. Preskill, S. H. Wagaw, S. J. Wittenberger and J. Zhang, J. Am. Chem. Soc. 2002, 124, 13097.
7. (b) Y. Hoashi, T. Yabuta and Y. Takemoto, Tetrahedron Lett. 2004, 45, 9185.
8. (a) J. G. Ji, D. M. Barnes, J. Zhang, S. A. King, S. J. Wittenberger and H. E. Morton, J. Am. Chem Soc. 1999, 121, 10215.
9. (b) M. Watanabe, A. Ikagawa, H. Wang, K. Murata and T. Ikarija. J. Am. Chem. Soc. 2004, 126, 11148.
10. For some reviews see: (a) P. I. Dalko and L. Moisan, Angew. Chem., Int. Ed, 2001, 40, 3726.
11. (b) P. I. Dalko and L. Moisan. Angew. Chem., Int. Ed, 2004, 43, 5138.
12. (c) A. Berkessel and H. Groger. Asymmetric Organocatalysis, VCH. Weinheim. 2004.
13. (d) I. Seayad and B. List. Org. Biomol, Chem., 2005, 3, 719.
14. (a) B. List, P. Pojarliev and H. J. Martin, Org. Lett. 2001, 3, 2423.
15. (b) J. M. Betancort and C. F. Barbas III, Org. Lett., 2001, 3, 3737.
16. (c) A. Alexakis and O. Andrey, Org. Lett. 2002, 4, 3611.
17. (d) D. Enders and A. Seki, Synlett, 2002, 26.
18. (e) O. Audrey, A. Alexakis and G. Bernardinelli, Org. Lett., 2003, 5, 2559.
19. (f) T. Ishii, S. Fujioka, Y. Sekiguchi and H. Kotsuki, J. Am Chem Soc., 2004, 126, 9558.
20. (g) N. Mase, R. Thayumanavan, F. Tanaka and C. F. Barbas III. Org. Lett., 2004, 6, 2527.
21. (h) A. J. A. Cobb, D. A. Lonnbottom, D. M. Shaw and S. V. Ley. Chem Commun., 2004, 1808.
22. (i) C. H. T. Mitchell, A. J. A. Cobb and S. V. Ley, Synlett, 2005, 611.
23. (j) W. Wang, J. Wang and H. Li, Angew. Chem., Int. Ed., 2005, 44, 1369.
24. (a) H. Wynberg and A. A. Smaardijk, Tetrahedrom Lett., 1983, 24, 5899.
25. (b) J. I. Oku and S. Inoue, J. Chem. Soc., Chem. Commun. 1981, 229.
26. (c) K. Tanaka, A. Mori and S. Inoue. J. Org. Chem., 1990, 55, 181.
27. (d) Y. Iwabuchi, M. Nakatani, N. Yokoyamu and S. Hatakeyama, J. Am. Chem. Soc., 1999, 121, 10219.
28. (e) B. List, R. A Lerner and C. F. Barbas, J. Am. Chem. Soc., 2000, 122, 2395.
29. (f) A. B. Northrup and D. W. C. MacMillan, J. Am. Chem. Soc., 2002, 124, 6798.
30. (g) A. B. Norlhrup and D. W. C. MacMillan, Science. 2004, 305, 1753.
31. (a) M. S. Iyer, K. M. Gigstad, N. D. Namdev and M. Lipton, J. Am. Chem. Soc. 1996, 118, 4910;
32. (b) M. S. Sigman and E. N. Jacobsen, J. Am. Chem. Soc., 1998, 120, 4901;
33. (c) E. J. Corey and M. J. Grogan, Org. Lett., 1999, 1, 157;
34. (d) P. Vachal and E. N. Jacobsen, J. Am. Chem. Soc., 2002, 124, 10012;
35. (e) T. Okino, S. Nakamura, T. Furukawa and Y. Takemoto, Org. Lett., 2004, 6, 625;
36. (f) B. M. Nugent, R. A. Yoder and J. N. Johnston, J. Am. Chem. Soc., 2004, 126, 3418;
37. (g) G. D. Joly and E. N. Jacobsen, J. Am. Chem. Soc., 2004, 126, 4102;
38. (h) K. Matsui, S. Takizawa and H. Sasai, J. Am. Chem. Soc., 2005, 127, 3680.
39. (a) T. E. Horstmann, D. J. Guerin and S. J. Miller, Angew. Chem., Int. Ed. 2000, 39, 3635;
40. (b) T. Okino, Y. Hoashi and Y. Takemoto, J. Am. Chem. Soc., 2003, 125, 12672;
41. (c) T. Okino, Y. Hoashi, T. Furukawa, X. Xu and Y. Takemoto, J. Am. Chem. Soc., 2005, 127, 119;
42. (d) H. Li, Y. Wang, L. Tang and L. Deng, J. Am. Chem. Soc., 2004, 126, 9906;
43. (e) H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman and L. Deng, Angew. Chem., Int. Ed., 2005, 44, 105;
44. (f) H. Li, J. Song, X. Liu and L. Deng, J. Am. Chem Soc., 2005, 127, 8948.
45. (a) S. P. Brown, M. P. Brochu, C. J. Sinz and D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808;
46. (b) S. Saaby, M. Bella and K. A. Jorgensen, J. Am. Chem. Soc. 2004, 126, 8120;
47. (c) A. Berkessel, F. Cleemann, S. Mukherjee, T. N. Müller and J. Lex, Angew. Chem., Int. Ed., 2005, 44, 807;
48. (d) A. Berkessel, S. Mukherjee, F. Cleemann, T. N. Müller and J. Lex, Chem. Commun. 2005, 1898;
49. (e) X. Liu, H. Li and L. Deng, Org. Lett., 2005, 7, 167.
50. For some reviews on bifunctional or multifunctional asymmetric catalysis and dual activation of substrates and reagents see: (a) M. Sawamura and Y. Iyo, Chem. Rev., 1992, 92, 857;
51. (b) H. Steinhagen and G. Helmchen, Angew. Chem., Int. Ed. Engl., 1996, 35, 2339;
52. (c) M. Shibasaki, H. Sasai and T. Arai, Angew. Chem., Int. Ed. Engl. 1997, 36, 1237;
53. (d) E. K. van den Beuken and B. L. Feringa, Tetrahedron. 1998, 54, 12985;
54. (e) M. Shibasaki and M. Kanai, Chem. Pharm. Bull., 2001, 49, 511;
55. (f) G. J. Rowlands, Tetrahedron, 2001, 57, 1865;
56. (g) M. Shibasaki and N. Yoshikawa, Chem. Rev., 2002, 102, 2187;
57. (h) J.-A. Ma and D. Canard, Angew. Chem., Int. Ed., 2004, 43, 4566.
58. For the synthesis and application of 9-amino(9-deoxy) epi-Cinchona alkaloids see: (a) H. Brunner, J. Bügler and B. Nuber, Tetrahedron: Asymmetry, 1995, 6, 1699;
59. (b) H. Brunner and J. Buegler, Bull. Soc. Chim. Belg., 1997, 106, 77;
60. (c) H. Brunner, P. Schmidt and M. Prommesberger, Tetrahedron: Asymmetry, 2000, 11, 1501;
61. (d) H. Brunner and P. Schmidt, Eur. J. Org. Chem., 2000, 2119;
62. (e) H. Brunner and M. A. Baur, Eur. J. Org. Chem., 2003, 2854.
63. During the preparation of this manuscript Chen et al. reported the asymmetric Michael addition of phenylthiol to an unsaturated imide acceptor with 17% ee using a related catalyst, see: (a) B. J. Li, L. Jiang, M. Liu, Y. C. Chen, L. S. Ding and Y. Wu, Synlett. 2005, 603;
64. Soós et al. have recently reported the asymmetric Michael addition of nitromethane to chalcones catalysed by a chiral thiourea derived from 9-amino-9-deoxy epiquinine and 9-amino-9-deoxy epiquindine, see: (b) B. Vakulya, S. Varga, A. Csampa and T. Soós, Org. Lett., 2005, 7, 1967.
65. (a) T. P. Yoon and E. N. Jacobsen, Science, 2003, 299, 1691;
66. (b) K. Kaeprzak and J. Gawroñski, Synthesis, 2001, 961.