Modularly designed organocatalytic assemblies for direct nitro-Michael addition reactions

Angewandte Chemie - International Edition

Volumn 47, Issue 40, 2008, Pages 7714-7717

  Mandal, Tanmay ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

Alkaloids; Amino acids; Asymmetric synthesis; Michael addition; Organocatalysis; Self assembly

Indexed keywords

EID: 54749140370     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803236     Document Type: Article

References (73)

1. For reviews, see: a) A. Berkessel, H. Groeger in Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005;
2. b) H. Pellissier, Tetrahedron 2007, 63, 9267-9331.
3. For reviews, see: a) S. V. Ley, Tetrahedron: Asymmetry 2007, 201-206;
4. b) W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580-591;
5. c) B. List, Tetrahedron 2002, 58, 5573-5590.
6. M. L. Clarke, J. A. Fuentes, Angew. Chem. 2007, 119, 948-951;
7. Angew. Chem. Int. Ed. 2007, 46, 930-933.
8. For reviews, see a) C. Gennari, U. Piarulli, Chem. Rev. 2003, 103, 3071-3100;
9. b) M. T. Reetz, Angew. Chem. 2001, 113, 292-320;
10. Angew. Chem. Int. Ed. 2001, 40, 284-310;
11. c) B. Breit, Angew. Chem. 2005, 117, 6976-6986;
12. Angew. Chem. Int. Ed. 2005, 44, 6816-6825.
13. For some leading examples using modular approach in designing transition metal catalysts, see: d) B. Breit, W. Seiche, Angew. Chem. 2005, 117, 1666-1669;
14. Angew. Chem. Int. Ed. 2005, 44, 1640-1643;
15. e) M. Weis, C. Waloch, W. Seiche, B. Breit, J. Am. Chem. Soc. 2006, 128, 4188-4189;
16. f) F. Chevallier, B. Breit, Angew. Chem. 2006, 118, 1629-1632;
17. Angew. Chem. Int. Ed. 2006, 45, 1599-1602;
18. g) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523;
19. Angew. Chem. Int. Ed. 1999, 38, 497-501;
20. h) F. W. Patureau, M. Kuil, A. J. Sandee, J. N. H. Reek, Angew. Chem. 2008, 120, 3224-3227;
21. Angew. Chem. Int. Ed. 2008, 47, 3180-3183;
22. i) X.-B. Jiang, L. Lefort, P. E. Goudriaan, A. H. M. de Vries, P. W. N. M. van Leeuwen, J. G. de Vries, J. N. H. Reek, Angew. Chem. 2006, 118, 1245-1249;
23. Angew. Chem. Int. Ed. 2006, 45, 1223-1227;
24. j) V. F. Slagt, M. Roeder, P. C. J. Kamer, P. W. N. M. Van Leeuwen, J. N. H. Reek, J. Am. Chem. Soc. 2004, 126, 4056-4057.
25. a) T. Mandal, S. Samanta, C.-G. Zhao, Org. Lett. 2007, 9, 943-945;
26. b) R. Dodda, J. J. Goldman, T. Mandal, C.-G. Zhao, G. A. Broker, E. R. T. Tiekink, Adv. Syn. Catal. 2008, 350, 537-541;
27. c) R. Dodda, T. Mandal, C.-G. Zhao, Tetrahedron Lett. 2008, 49, 1899-1902.
28. For some leading examples of quinine derivative-catalyzed reactions, see: a) H. Li, B. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 732-733;
29. b) L. Zu, J. Wang, H. Li, H. Xie, W. Jiang, W. Wang, J. Am. Chem. Soc. 2007, 129, 1036-1037;
30. c) M. M. Biddle, M. Lin, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 3830-3831;
31. d) H. Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906-9907;
32. e) M. Bella, K. A. Jorgensen, J. Am. Chem. Soc. 2004, 126, 5672-5673;
33. f) G. Bartoli, M. Bosco, A. Carlone, A. Cavalli, M. Locatelli, A. Mazzanti, P. Ricci, L. Sambri, P. Melchiorre, Angew. Chem. 2006, 118, 5088-5092;
34. Angew. Chem. Int. Ed. 2006, 45, 4966-4970.
35. For a review, see: A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743.
36. For leading examples of using chiral ammonium salts for asymmetric counteranion-directed catalysis, see: a) N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368-13369;
37. b) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299-4301;
38. Angew. Chem. Int. Ed. 2006, 45, 4193-4195.
39. For an example of using carboxylic acid as an additive in the quinine derivative-catalyzed nitro-Michael reaction, see: S. H. McCooey, S. J. Cannon, Org. Lett. 2007, 9, 599-602.
40. For examples of self-assembly between amines and acids, see: a) C. Schmuck, W. Wienand, J. Am. Chem. Soc. 2003, 125, 452-459;
41. b) S. Le Gac, M. Luhmer, O. Reinaud, I. Jabin, Tetrahedron 2007, 63, 10721-10730.
42. For a review, see: P. Perlmutter in Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
43. For some leading examples, see: a) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287;
44. Angew. Chem. Int. Ed. 2005, 44, 4212-4215;
45. b) W. Wang, J. Wang, H. Li, Angew. Chem. 2005, 117, 1393-1395;
46. Angew. Chem. Int. Ed. 2005, 44, 1369-1371;
47. c) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966-4967;
48. d) S. V. Pansare, K. J. Pandya, J. Am. Chem. Soc. 2006, 128, 9624-9625;
49. e) L. Zu, J. Wang, H. Li, W. Wang, Org. Lett. 2006, 8, 3077-3079;
50. f) C. Palomo, S. Vera, A. Mielgo, E. Gomóz-Bengoa, Angew. Chem. 2006, 118, 6130-6133;
51. Angew. Chem. Int. Ed. 2006, 45, 5984-5987;
52. g) C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042-8046;
53. Angew. Chem. Int. Ed. 2006, 45, 7876-7880;
54. h) D. Enders, C. Huttl, M. R. M. Grondal, G. Raabe, Nature 2006, 441, 861-863;
55. i) S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451-1453;
56. j) H. Huang, E. N. Jacobsen, J. Am. Chem. Soc. 2006, 128, 7170-7171;
57. k) M. Wiesner, J. D. Revell, H. Wennemers, Angew. Chem. 2008, 120, 1897-1900;
58. Angew. Chem. Int. Ed. 2008, 47, 1871-1874;
59. l) P. García-García, A. Ladépêche, R. Halder, B. List, Angew. Chem. 2008, 120, 4797-4799;
60. Angew. Chem. Int. Ed. 2008, 47, 4719-4721;
61. m) Y. Hayashi, T. Itoh, M. Ohkubo, H. Ishikawa, Angew. Chem. 2008, 120, 4800-4802;
62. Angew. Chem. Int. Ed. 2008, 47, 4722-4724;
63. n) M. Wiesner, J. D. Revell, S. Tonazzi, H. Wennemers, J. Am. Chem. Soc. 2008, 130, 5610-5611;
64. o) Y. Chi, L. Guo, N. A. Kopf, S. H. Gellman, J. Am. Chem. Soc. 2008, 130, 5608-5609.
65. For reviews, see: p) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1706;
66. q) D. Almaşi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299-365.
67. a) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2424;
68. b) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444;
69. c) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267;
70. d) D. Enders, A. Seki, Synlett 2002, 26-28.
71. For more details, please see the Supporting Information.
72. S. B. Tsogoeva, S. B. Jagtap, Synlett 2004, 2624-2626.
73. For a list of additional substrates, please see Tables 6 and 7 in the Supporting Information.