Chiral bicyclic guanidine as a versatile brønsted base catalyst for the enantioselective michael reactions of dithiomalonates and β-keto thioesters

Advanced Synthesis and Catalysis

Volumn 349, Issue 16, 2007, Pages 2454-2458

  Ye, Weiping ^a   Jiang, Zhiyong ^a   Zhao, Yujun ^a   Goh, Serena Li Min ^a   Leow, Dasheng ^a   Soh, Ying Teck ^a   Tan, Choon Hong ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Asymmetric catalysis; Dithiomalonates; Guanidines; Michael addition; Organic catalysis

Indexed keywords

EID: 36749034757     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700326     Document Type: Article

References (88)

1. a) Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
2. b) R. Ballini, G. Bosica, D. Fiorini, A. Palmeiri, M. Petrini, Chem. Rev. 2005, 105, 933-971;
3. c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894;
4. d) M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269-279;
5. e) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196;
6. f) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061.
7. a) H. Sasai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1994, 116, 1571-1572;
8. b) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996, 108, 103-105;
9. Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106;
10. c) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507;
11. d) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240-11241;
12. e) M. Watanabe, A. Ikagawa, H. Wang, K. Murata, T. Ikariya, J. Am. Chem. Soc. 2004, 126, 11148-11149;
13. f) J. Ji, D. M. Barnes, J. Zhang, S. A. King, S. J. Wittenburger, H. E. Morton, J. Am. Chem. Soc. 1999, 121, 10215-10216;
14. g) D. A. Evans, D. Seidel, J. Am. Chem. Soc. 2005, 127, 9958-9959.
15. a) A. Berkessel, H. Gröger, Asymmetric Organocatalysis-From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weunheim, 2005, pp47-55;
16. b) J. Seayad, B. List, Org. Biomol Chem. 2005, 3, 719-724;
17. c) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286;
18. Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
19. d) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840-3864;
20. Angew. Chem. Int. Ed. 2001, 40, 3726-3748.
21. a) N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 5105-5107;
22. Angew. Chem. Int. Ed. 2003, 42, 4955-4957;
23. b) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685-689;
24. Angew. Chem. Int. Ed. 2003, 42, 661-665.
25. a) T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119-125;
26. b) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673;
27. c) S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525-6528;
28. Angew. Chem. Int. Ed. 2005, 44, 6367-6370;
29. d) J. Wang, H. Li, W. Duan, L. Zu, W. Wang, Org. Lett. 2005, 7, 4713-4716;
30. e) J. Wang, H. Li, L. Zu. W. Jiang, H. Xie, W. Duan, W. Wang, J. Am. Chem. Soc. 2006, 128, 12652-12653;
31. f) J. Ye, D. J. Dixon, P. S. Hynes, Chem. Commun. 2005, 4481-4483.
32. a) H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2004, 117, 107-110;
33. Angew. Chem. Int. Ed. 2005, 44, 105-108;
34. b) H. Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906-9907;
35. c) F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. 2006, 118, 4407-4411;
36. Angew. Chem. Int. Ed. 2006, 45, 947-950;
37. d) M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 5672-5673;
38. e) G. Bartoli, M. Bosco, A. Carlone, A. Cavalli, M. Locatelli, A. Mazzanti, P. Ricci, L. Sambri, P. Melchiorre, Angew. Chem. 2006, 118, 5088-5092;
39. Angew. Chem. Int. Ed. 2006, 45, 4966-4970.
40. a) T. Ooi, T. Miki, M. Taniguchi, M. Shiraishi, M. Takeuchi, K. Maruoka, Angew. Chem. 2003, 115, 3926-3928;
41. Angew. Chem. Int. Ed. 2003, 115, 3796-3798;
42. b) T. Ooi, D. Ohara, K. Fukumoto, K. Maruoka, Org. Lett. 2005, 7, 3195-3197.
43. K. R. Knudsen, C. E. T. Mitchell, S. V. Ley, Chem. Commun. 2006, 66-68.
44. a) M. S. Iyer, K. M. Gigstad, N. D. Namdev, M. Lipton, J. Am. Chem. Soc. 1996, 118, 4910-4911;
45. b) E. J. Corey, M. Grogan, J. Org. Lett. 1999, 1, 157-160.
46. a) T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552-557;
47. b) T. Ishikawa, Y. Araki, T. Kumamoto, H. Seki, K. Fukuda, T. Isobe, Chem. Commun. 2001, 245-246;
48. c) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956-2958;
49. Angew. Chem. Int. Ed. 2002, 41, 2832-2834;
50. d) M. T. Allingham, A. Howard-Jones, P. J. Murphy, D. A. Thomas, P. W. R. Caulkett, Tetrahedron Lett. 2003, 44, 8677-8680;
51. e) Y. Sohtome, Y. Hashimoto, K. Nagasawa, Adv. Synth. Catal. 2005, 347, 1643-1648.
52. a) M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454-1455;
53. b) M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044-16045.
54. J. Shen, T. T. Nguyen, Y.-P. Goh, W. Ye, X. Fu, J. Xu, C.-H. Tan, J. Am. Chem. Soc. 2006, 128, 13692-13693.
55. a) Y. Takaya, T. Senda, H. Kurushima, M. Ogasawara, T. Hayashi, Tetrahedron: Asymmetry 1999, 10, 4047-4056;
56. b) S. Sakuma, M. Sakai, R. Itooka, N. Miyaura, J. Org. Chem. 2000, 65, 5951-5955.
57. For biological activities of homo-β-proline, see: a) D. R. IV Coleman, Z. Ren, P. K. Mandai, A. G. Cameron, G. A. Dyer, S. Muranjan, M. Campbell, X. Chen, J. S. McMurray, J. Med. Chem. 2005, 48, 6661-6670;
58. b) K. E. Andersen, J. L. Sørensen, J. Lau, B. F. Lundt, H. Petersen, P. O. Huusfeldt, P. D. Suzdak, M. D. B. Swedberg, J. Med. Chem. 2001, 44, 2152-2163;
59. c) V. N'Goka, G. Schiewer, J.-M. Linget, J.-P. Chambon, C.-G. Wermuth, J. Med. Chem. 1991, 34, 2547-2557;
60. d) L. Nielsen, L. Brehm, P. Krogsgaard-Larsen, J. Med. Chem. 1990, 33, 71-77;
61. e) L. M. Yunger, P. J. Fowler, P. Zarevics, P. E. Setler, J. Pharmacol. Exp. Ther. 1984, 228, 109-115.
62. a) N. G. Bowery, T. G. Smart, Br. J. Pharmacol. 2006, 147, S109-S119;
63. b) U. Rudolph, H. Möhler, Curr. Opin. Pharmacol. 2006, 6, 18-23.
64. F. Felluga, V. Gombac, G. Pitacco, E. Valentin, Tetrahedron: Asymmetry 2004, 15, 3323-3327.
65. a) R. Galeazzi, S. Geremia, G. Mobbili, M. Orena, Tetrahedron: Asymmetry 1996, 7, 79-88;
66. b) R. Galeazzi, G. Mobbili, M. Orena, Tetrahedron 1996, 52, 1069-1084.
67. C. Thomas, F. Orecher, P. Gmeiner, Synthesis 1998, 1491-1496.
68. a) Y. Mori, M. Seki, Tetrahedron Lett. 2004, 45, 7343-7345;
69. b) P. L. DeRoy, A. B. Charette, Org. Lett. 2003, 5, 4163-4165;
70. c) T. Fukuyama, S.-C. Lin, L. Li, J. Am. Chem. Soc 1990, 112, 7050-7051.
71. H.-J. Liu, I. V. Oppong, Can. J. Chem. 1982, 60, 94-96.
72. a) R. Shintani, W.-L. Duan, T. Nagano, A. Okada, T. Hayashi, Angew. Chem. 2005, 117, 4687-4690;
73. Angew. Chem. Int. Ed. 2005, 44, 4611-4614;
74. b) S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2582-2590;
75. c) J. K. Myers, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 8959-8960;
76. d) Y. Bi, L. Bailly, F. Marsais, V. Levacher, C. Papamicaël, G. Dupas, Tetrahedron: Asymmetry 2004, 15, 3703-3706;
77. e) R. Ballini, G. Bosica, G. Cioci, D. Fiorini, M. Petrini, Tetrahedron 2003, 59, 3603-3608;
78. f) J. H. Nelson, P. N. Howells, G. C. DeLullo, G. L. Landen, J. Org. Chem. 1980, 45, 1246-1249.
79. a) J. Pohlmann, T. Lampe, M. Shimada, P. G. Nell, J. Pernerstorfer, N. Svenstrup, N. A. Brunner, Bioorg. Med. Chem. Lett. 2005, 15, 1189-1192;
80. b) M. L. Curtin, R. B. Garland, H. R. Heyman, R. R. Frey, M. R. Michaelides, J. Li, L. J. Pease, K. B. Glaser, P. A. Marcotte, S. K. Davidsen, Bioorg. Med. Chem. Lett. 2002, 12, 2919-2923.
81. a) A. Mitchinson, A. Nadin, J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892;
82. b) M. Pichon, B. Figadère, Tetrahedron: Asymmetry 1996, 77, 927-964.
83. A. R. Katritky, J. Yao, M. Qi, Y. Chou, D. J. Sikora, S. Davis, Heterocycles, 1998, 48, 2677-2691.
84. a) C. E. T. Mitchell, S. E. Brenner, S. V. Ley, Chem. Commun. 2005, 5346-5348;
85. b) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978;
86. c) M. Yamaguchi, T. Shiraishi, M. Hirama, J. Org. Chem. 1996, 61, 3520-3530.
87. a) S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192-1194;
88. b) C. E. T. Mitchell, S. E. Brenner, J. García-Fortanet, S. V. Ley, Org. Biomol. Chem. 2006, 4, 2039-2049.