Chiral amine thiourea-promoted enantioselective domino Michael-aldol reactions between 2-mercaptobenzaldehydes and maleimides

Advanced Synthesis and Catalysis

Volumn 349, Issue 11-12, 2007, Pages 1882-1886

  Zu, Liansuo ^a   Xie, Hexin ^a   Li, Hao ^a   Wang, Jian ^a   Jiang, Wei ^a   Wang, Wei ^a  

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Michael addition; Organic catalysis

Indexed keywords

EID: 34548388318     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700158     Document Type: Article

References (73)

1. a) S. Ahmed, Drug Des. Discovery 1996, 14, 77;
2. b) A. R. Katritzky, J. Yao, M. Qi, Y. Chou, D. J. Sikora, S. Davis, Heterocycles 1998, 48, 2677;
3. c) R. Ballini, G. Bosica, G. Cioci, D. Fiorini, M. Petrini, Tetrahedron 2003, 59, 3603.
4. Examples of drugs containing succinimide moieties include Bradycor, Tandospirone, Buspirone, and Azimilide.
5. Reviews regarding the synthesis and biological application of benzothiopyrans, see: a) A. H. Ingall, in: Comprehensive Hetreocyclic Chemistry II, (Eds. : A. S. Boulton, A. McKillop), Pergamon Press: Oxford, 1996; Vol. 5, p 501;
6. b) S. W. Schneller, Adv. Heterocycl. Chem. 1975, 18, 59;
7. c) A. R. Katrizky, A. J. Bonlton, Adv. Heterocycl. Chem. 1975, 18, 76.
8. Reviews of asymmetric catalysis by H-bonding interactions, see: a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289;
9. b) S.-K. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 521;
10. c) Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299;
11. d) M. S. Taylor, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 1520;
12. e) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999;
13. f) S. J. Connon, Chem. Eur. J. 2006, 12, 5418.
14. Recently, we have developed organocatalytic domino Michael-aldol processes, see: a) L.-S. Zu, J. Wang, H. Li, H.-X. Xie, W. Jiang, W. Wang, J. Am. Chem. Soc. 2007, 129, 1036;
15. b) H. Li, J. Wang, H.-X. Xie, L.-S. Zu, W. Jiang, E. N. Duesler, W. Wang, Org. Lett. 2007, 9, 965;
16. c) H. Li, J. Wang, T. E-Nunu, L.-S. Zu, W. Jiang, S.-H. Wei, W. Wang, Chem. Commun. 2007, 507;
17. d) W. Wang, H. Li, J. Wang, L.-S. Zu, J. Am. Chem. Soc. 2006, 128, 10354.
18. A. Berkessel, H. Gröger, Asymmetric Organocatalysis - From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005.
19. For selected reviews of organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138;
20. b) special issue on asymmetric organocatalysis: Acc. Chem. Res. 2004, 37, 487.
21. For recent reviews of tandem reactions, see: a) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
22. b) C. Palomo, A. Mielgo, Angew. Chem. Int. Ed. 2006, 45, 7876;
23. c) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. Int. Ed. 2006, 45, 7134;
24. d) H. Guo, J. Ma, Angew. Chem. Int. Ed. 2006, 45, 354;
25. e) H. Pellissier, Tetrahedron 2006, 62, 2143;
26. f) L. F. Tietze, Chem. Rev. 1996, 96, 115.
27. For selected examples of organocatalytic tandem reactions, see: a) T. Dudding, A. M. Hafez, A. E. Taggi, T. R. Wagerle, T. Lectka, Org. Lett. 2002, 4, 387;
28. b) D. B. Ramachary, N. S. Chowdari, C. F. Barbas, III Angew. Chem. Int. Ed. 2003, 42, 4233;
29. c) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962;
30. d) M. Marigo, T. Schulte, J. Franzen, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15710;
31. e) J. Casas, M. Engqvist, I. Ibrahem, B. Kaynak, A. Córdova, Angew. Chem. Int. Ed. 2005, 44, 1343;
32. f) J. W. Yang, M. T. Hechavarria Fonseca, B. List, J. Am. Chem. Soc. 2005, 127, 15036;
33. g) Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051;
34. h) Y. Wang, X.-F. Liu, L. Deng, J. Am. Chem. Soc. 2006, 128, 3928;
35. i) D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861;
36. j) D. Enders, M. R. M. Hüttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. Int. Ed. 2007, 46, 467;
37. k) B. Wang, F. Wu, Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2007, 129, 768.
38. For selected examples of organocatalytic asymmetric Michael addition of enones, see: a) H. Hiemstra, H. Wynberg, J. Am. Chem. Soc. 1981, 103, 417;
39. b) E. J. Corey, F.-Y. Zhang, Org. Lett. 2000, 2, 4257;
40. c) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975;
41. d) N. Halland, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67, 8331;
42. e) T. Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 9022;
43. f) B. Bakulya, S. Varga, A. Csámpai, T. Sóos, Org. Lett. 2005, 7, 1967;
44. g) F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. Int. Ed. 2006, 45, 947;
45. h) F. Wu, R. Hong, J. Khan, X. Liu, L. Deng, Angew. Chem. Int. Ed. 2006, 45, 4301;
46. i) J. Wang, H. Li, L.-S. Zu, W Jiang, H.-X. Xie, W.-H. Duan, W. Wang, J. Am. Chem. Soc. 2006, 128, 12652;
47. j) J. Wang, H. Li, L.-S. Zu, W. Wang, Adv. Synth. Catal. 2006, 348, 425.
48. For selected examples of organocatalytic asymmetric Michael addition of nitroolefins, see: a) J. M. Betancort, C. F. Barbas, III. Org. Lett. 2001, 3, 3737;
49. b) D. Enders, A. Seki, Synlett 2002, 26;
50. c) O. Andrey, A. Alexakis, G. Bernardinelli, Org. Lett. 2003, 5, 2559;
51. d) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672;
52. e) T. Ishii, S. Fiujioka, Y. Sekiguchi, H. Kotsuki, J. Am. Chem. Soc. 2004, 126, 9558;
53. f) A. J. A. Cobb, D. A. Longbottom, D. M. Shaw, S. V. Ley, Chem. Commun. 2004, 1808;
54. g) T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119;
55. h) Y. Hayashi, T. Gotoh, T. Hayasji, M. Shoji, Angew. Chem. Int. Ed. 2005, 44, 4212;
56. i) R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. Int. Ed. 2005, 44, 6576;
57. j) S. B. Tsogoeva, D. A. Yalalov, M. J. Hateley, C. Weckbecker, K. Huthmacher, Eur. J. Org. Chem. 2005, 4995;
58. k) S. H. McCooey, S. J. Connon, Angew. Chem. Int. Ed. 2005, 44, 6367;
59. l) J. Wang, H. Li, W. Duan, L. Zu, W. Wang, Org. Lett. 2005, 7, 4713;
60. m) J. Ye, D. J. Dixon, P. S. Hynes, Chem. Commun. 2005, 4481;
61. n) H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, Deng, Li. Angew. Chem. Int. Ed. 2005, 44, 105;
62. o) Y.-M. Xu, W.-B. Zou, H. Sunden, I. Ibrahem, A. Cordova, Adv. Synth. Catal. 2006, 348, 418;
63. p) M. P. Lalonde, Y. Chen, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 6366.
64. For examples of organocatalytic asymmetric Michael addition of imides, see: a) D. J. Guerin, S. J. Miller, J. Am. Chem. Soc 2002, 124, 2136;
65. b) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc 2003, 125, 11204;
66. c) Y. Hoashi, T. Okino, Y. Takemoto, Angew. Chem. Int. Ed. 2005, 44, 4032.
67. For examples of organocatalytic asymmetric Michael addition of sulfones, see: a) H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948;
68. b) S. Mossé, A. Alexandre, Org. Lett. 2005, 7, 4361.
69. a) R. Shintani, W.-L. Duan, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 5628;
70. b) G. Bartoli, M. Bosco, A. Carlone, A. Cavalli, M. Locatelli, A. Mazzanti, P. Ricci, L. Sambri, P. Melchiorre, Angew. Chem. Int. Ed. 2006, 45, 4966;
71. c) G.-L. Zhao, Y. Xu, H. Sundén, L. Eriksson, M. Sayah, A. Córdova, Chem. Commun. 2007, 734.
72. CCDC-640708 contains the supplementary crystallography data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk.
73. A. Hamza, G. Schubert, T. Soós, I. Pápai, J. Am. Chem. Soc. 2006, 128, 13151.