Asymmetric organocatalytic domino Michael/aldol reactions: Enantioselective synthesis of chiral cycloheptanones, tetrahydrochromenones, and polyfunctionalized bicyclo-[3.2.1]octanes

Angewandte Chemie - International Edition

Volumn 48, Issue 20, 2009, Pages 3699-3702

  Rueping, Magnus ^a   Kuenkel, Alexander ^a   Tato, Francisco ^a   Bats, Jan W ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

Aldol reaction; Domino reaction; Michael addition; Organocatalysis; Prolinol ethers

Indexed keywords

ALDOL REACTION; DOMINO REACTION; MICHAEL ADDITION; ORGANOCATALYSIS; PROLINOL ETHERS;

ADDITION REACTIONS; ALDEHYDES; CATALYSIS; ENANTIOSELECTIVITY; ETHERS; RATE CONSTANTS; SYNTHESIS (CHEMICAL);

REACTION KINETICS;

EID: 70349777755     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900754     Document Type: Article

References (100)

1. Selected examples for the application of 1, 2-diones in organic synthesis: a) A. F. Parsons, D. Williams, Tetrahedron 2000, 56, 7217;
2. b)C. Wolf, S. Liu, J. Am. Chem. Soc. 2006, 128, 10996;
3. c) C. W Lindsley, D. D. Wisnoski, Y. Wang, W H. Leister, Z. Zhao, Tetrahedron Lett. 2003, 44, 4495;
4. d) X. Li, R. Vince, Bioorg. Med. Chem. 2006, 14, 2942;
5. e) H. Maruoka, N. Kashige, F. Miake, T. Yamaguchi, Chem. Pharm. Bull. 2005, 53, 1359;
6. f) Z. Zhao, D. D. Wisnoski, S. E. Wolkenberg, W H. Leister, Y Wang, C. W Lindsley, Tetrahedron Lett. 2004, 45, 4873;
7. g) E. Dubost, D. Le Nouen, J. Streith, C. Tarnus, T. Tschamber, Eur. J. Org. Chem. 2006, z.ast;610;
8. h) D. Curiel, A. Cowley, P. D. Beer, Chem. Commun. 2005, 236;
9. i) Y Ding, J. Girardet, K. L. Smith, G. Larson, B. Prigaro, V. C. H. Lai, W Zhong, J. Z. Wu, Bioorg. Med. Chem. Lett. 2005, 15, 675;
10. j) S. Wu, A. Fluxe, J. M. Janusz, J. B. Sheffer, G Browning, B. Blass, K. Cobum, R. Hedges, M. Murawsky, B. Fang, G M. Fadayel, M. Hare, L. Djandjighian, Bioorg. Med. Chem. Lett. 2006, 16, 5859;
11. k) I. Held, S. Xu, H. Zipse, Synthesis 2007, z.ast;1185;
12. l) S. Liu, C. Wolf, Org. Lett. 2007, 9, 2965;
13. m) A. Svennebring, P. Nilsson, M. Larhed,J. Org. Chem. 2007, 72, 5851;
14. n) B. M. Trost, G M. Schroeder, J. Am. Chem. Soc. 2000, 122, 3785;
15. o) V. Nair, S. Vellalath, M. Poonoth, R. Mohan, E. Suresh, Org. Lett. 2006, 8, 507;
16. p) T. Schuster, M. Bauch, G Durner, M. Gobel, Org. Lett. 2000, 2, 179.
17. a) M. Rueping, E. Sugiono, E. Merino, Angew. Chem. 2008, 120, 3089;
18. Angew. Chem. Int. Ed. 2008, 47, 3046;
19. b) M. Rueping, E. Sugiono, E. Merino, Chem. Eur. J. 2008, 14, 6329;
20. c) M. Rueping, E. Merino, E. Sugiono, Adv. Synth. Catal. 2008, 350, 2127.
21. Use of 1, 2-diones as electrophile in an organocatalytic aldol reaction: S. Samanta, C. Zhao, Tetrahedron Lett. 2006, 47, 3383.
22. a)M. Utaka, Y Fujii, A. Takeda, Chem. Lett. 1985, 1123;
23. b) H. O. House, B. M. Trost, R. W Magin, R. G Carlson, R. W. Franck, G H. Rasmusson, J. Org. Chem. 1965, 30, 2513;
24. c) H. Hagiwara, K. Sato, D. Nishino, T. Hoshi, T. Suzuki, M . Ando, / Chem. Soc. Perkin Trans. 1 2001, 2946.
25. Selected examples of asymmetric domino reactions employing Lewis base catalysis: a) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951;
26. b) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292;
27. Angew. Chem. Int. Ed. 2004, 43, 1272;
28. c) J. W Yang, M. T. Hechavarria Fonsecca, B. List, J. Am. Chem. Soc. 2005, 127, 15036;
29. d) Y Huang, A. M. Walji, C. H. Larsen, D. W C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051;
30. e) M. Marigo, T. Schulte, J. Franzen, K. A. J0rgensen, J. Am. Chem. Soc. 2005, 127, 15710;
31. f) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354;
32. g) R. K. Kunz, D. W C. MacMillan, J. Am. Chem. Soc. 2005, 127, 3240;
33. h) M. Marigo, J. Franzen, T. B. Poulsen, W Zhuang, K. A. J0rgensen, J. Am. Chem. Soc. 2005, 127, 6964;
34. i) S. Brandau, E. Maerten, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 14986;
35. j) L. Zu, H. Li, H. Xie, J. Wang, W Jiang, Y. Tang, W Wang, Angew. Chem. 2007, 119, 3806;
36. Angew. Chem. Int. Ed. 2007, 46, 3732;
37. k) J. Wang, H. Li, H. Xie, L. Zu, X. Shen, W Wang, Angew. Chem. 2007, 119, 9208;
38. Angew. Chem. Int. Ed. 2007, 46, 9050;
39. l) H. Xie, L. Xu, H. Li, J. Wang, W Wang, J. Am. Chem. Soc. 2007, 129, 10886;
40. m) R. Rios, J. Vesely, H. Sunden, G. Zhao, P. Dziedzic, A. Cordova, Adv. Synth. Catal. 2007, 349, 1028;
41. n) H. Li, L. Zu, H. Xie, J. Wang, W Jiang, W Wang, Org. Lett. 2007, 9, 1833;
42. o) B. Hong, R. Y. Nimje, A. A. Sadani, J. Liao, Org. Lett. 2008, 10, 2345;
43. p) D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006, 441, 861;
44. q) D. Enders, M. R. M. Huttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. 2007, 119, 471;
45. Angew. Chem. Int. Ed. 2007, 46, 467;
46. r) Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010;
47. Angew. Chem. Int. Ed. 2007, 46, 4922;
48. s) J. L. Vicario, S. Reboredo, D. Badia, L. Carrillo, Angew. Chem. 2007, 119, 5260;
49. Angew. Chem. Int. Ed. 2007, 46, 5168;
50. t) E. Reyes, H. Jiang, A. Milelli, P. Elsner, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2007, 119, 9362;
51. Angew. Chem. Int. Ed. 2007, 46, 9202;
52. u) D. Hazelard, H. Ishikawa, D. Hashizume, H. Koshino, Y Hayashi, Org. Lett. 2008, 10, 1445;
53. v) O. Penon, A. Carlone, A. Mazzanti, M. Locatelli, L. Sambri, G Bartoli, P. Melchiorre, Chem. Eur. J. 2008, 14, 4788;
54. w) D. Enders, C. Wang, J. W Bats, Angew. Chem. 2008, 120, 7649;
55. Angew. Chem. Int. Ed. 2008, 47, 7539;
56. x) S. Bertelsen, R. L. Johansen, K. A. Jørgensen, Chem. Commun. 2008, 3018.
57. Reviews on domino reactions: a) L. F. Tietze, Chem. Rev. 1996, 96, 115;
58. b)J. Wasilke, S. J. Obrey, R. T. Baker, G C. Bazan, Chem. Rev. 2005, 105, 1001;
59. c) D. J. Ramon, M. Yus, Angew. Chem. 2005, 117, 1628;
60. Angew. Chem. Int. Ed. 2005, 44, 1602;
61. d) J. Zhu, H. Benayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005; e) L. F. Tietze, G Brasche, K. Gericke, Domino Reactions in Organic Synthesis Wiley-VCH, Weinheim, 2006; f) H. Guo, J. Ma, Angew. Chem. 2006, 118, 362;
62. Angew. Chem. Int. Ed. 2006, 45, 354;
63. g) H. Pellissier, Tetrahedron 2006, 62, 2143;
64. h)K. C. Nicolaou, D. J. Edmonds, P. G Bulger, Angew. Chem. 2006, 118, 7292;
65. Angew. Chem. Int. Ed. 2006, 45, 7134;
66. i) C. J. Chapman, C. G Frost, Synthesis 2007, 1.
67. Reviews on organocatalytic domino reactions: a) D. Enders, C. Grondal, M. R. M. Huttl, Angew. Chem. 2007, 119, 1590;
68. Angew. Chem. Int. Ed. 2007, 46, 1570;
69. b) X. Yu, W Wang, Org. Biomol. Chem. 2008, 6, 2037.
70. Selected examples from our laboratory: a) M. Rueping, T. Theissmann, A. P. Antonchick, Synlett 2006, 1071;
71. b) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765;
72. Angew. Chem. Int. Ed. 2006, 45, 3683;
73. c) M. Rueping, C. Azap, Angew. Chem. 2006, 118, 7996;
74. Angew. Chem. Int. Ed. 2006, 45, 7832;
75. d) M. Rueping, A. P. Antonchick, Angew. Chem. 2007, 119, 4646;
76. Angew. Chem. Int. Ed. 2007, 46, 4562;
77. e) M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027;
78. Angew. Chem. Int. Ed. 2007, 46, 6903;
79. f) M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603;
80. Angew. Chem. Int. Ed. 2008, 47, 593;
81. g) M. Rueping, T. Theissmann, S. Raja, J. W Bats, Adv. Synth. Catal. 2008, 350, 1001;
82. h) M. Rueping, A. P. Antonchick, Angew. Chem. 2008, 120, 5920;
83. Angew. Chem. Int. Ed. 2008, 47, 5836;
84. i) M. Rueping, A. P. Antonchick, Angew. Chem. 2008, 120, 10244;
85. Angew. Chem. Int. Ed. 2008, 47, 10090;
86. j) M. Rueping, W Ieawsuwan, Adv. Synth. Catal. 2009, 351, 78.
87. For interesting structural insights into enamine and iminium salt formation, see: a) D. Seebach, A. K. Beck, D. M. Badine, M. Limbach, A. Eschenmoser, A. M. Treasurywala, R. Hobi, W. Prikoszovich, B. Lindner, Helv. Chim. Acta 2007, 90, 425;
88. b) D. Seebach, A. K. Beck, D. M. Badine, M. Limbach, A. Eschenmoser, A. M. Treasurywala, R. Hobi, Helv. Chim. Acta 2007, 90, 1999;
89. c) U. Groselj, W B. Schweizer, M.-O. Ebert, D. Seebach, Helv. Chim. Acta 2009, 92, 1.
90. I. Perez-Castro, O. Caamano, M. D. Garcia, F. Fernandez, C. Lopez, Synthesis 2007, 1385.
91. Examples of retro-aldol reactions: a) K. Murakami, H. Ohmiya, H. Yorimitsu, K. Oshima, Tetrahedron Lett. 2008, 49, 2388;
92. b) D. Gangani Niyaduropola, I. R. Davies, R. Wisedale, S. D. Bull, Eur. J. Org. Chem. 2007, 5487;
93. c) K. Oisaki, D. Zhao, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 7439;
94. d) A. Stelmakh. T. Stellfeld, M. Kalesse, Org. Lett. 2006, 8, 3485;
95. e) L. Peng, M. Ma, X. Zhang, S. Zhang, J. Wang, Tetrahedron Lett. 2006, 47, 8175;
96. f) M. E. Jung, S. J. Min, Tetrahedron Lett. 2004, 45, 6753;
97. g) F. Clerici, M. L. Gelmi, S. Pelligrino, T. Pilati, J. Org. Chem. 2003, 68, 5286;
98. h) K. L. Granberg, K. M. Edvinsson, K. Nilsson, Tetrahedron Lett. 1999, 40, 755;
99. i) N. Acton, A. Brossi, Helv. Chim. Acta 1980, 63, 1396.
100. CCDC-725318 (8) and CCDC-725317 (7) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.