Enantioselective synthesis of coumarins catalyzed by a bifunctional amine-thiourea catalyst

Chemistry - A European Journal

Volumn 16, Issue 44, 2010, Pages 13068-13071

  Gao, Yaojun ^a   Ren, Qiao ^a   Wang, Lei ^a   Wang, Jian ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

asymmetric catalysis; coumarins; Michael addition; organocatalysis; thioureas

Indexed keywords

ASYMMETRIC CATALYSIS; BIFUNCTIONAL; COUMARINS; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE MICHAEL ADDITION; ENANTIOSELECTIVE SYNTHESIS; HIGH YIELD; HYDROGEN BONDINGS; MICHAEL ADDITIONS; ORGANOCATALYSIS; SMALL MOLECULES;

ADDITION REACTIONS; RATE CONSTANTS; REACTION KINETICS; SYNTHESIS (CHEMICAL); THIOUREAS; UREA;

CATALYSIS;

EID: 78649286224     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002202     Document Type: Article

References (70)

1. For selected reviews, see
2. R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins, Wiley, New York 1982
3. The Handbook of Natural Flavonoids (Eds.:, J. B. Harborne, H. Baxter,), Wiley, Chichester (UK) 1999
4. I. Manolov, N. D. Danchev, Eur. J. Med. Chem. 1995, 30, 531
5. C. Mouli, T. Giridhar, R. D. Mohan, R. B. Reddy, J. Heterocycl. Chem. 1996, 33, 5
6. K. Rehse, W. Schinkel, Arch. Pharm. 1983, 316, 988
7. R. A. O'Reilly, New Engl. J. Med. 1976, 295, 354
8. L. B. Wingard, R. A. O'Reilly, G. Levy, Clin. Pharmacol. Ther. 1978, 23, 212
9. H. Y. Li, A. J. Robinson, J. Feaster, Tetrahedron Lett. 1996, 37, 1551
10. G. Cravotto, G. M. Nano, G. Palmisano, S. Tagliapietra, Tetrahedron: Asymmetry 2001, 12, 707
11. K. C. Fylaktakidou, D. J. Hadjipavlou-Litina, K. E. Litinas, D. N. Nicolaides, Curr. Pharm. Des. 2004, 10, 3813
12. J. R. S. Hoult, M. Paya, Gen. Pharmacol. 1996, 27, 713.
13. For selected reviews, see
14. T. Meinertz, W. Kasper, C. Kahl, E. Jahnchen, Br. J. Clin. Pharmacol. 1978, 5, 187
15. M. Ufer, Clin. Pharmacokinet. 2005, 44, 1227
16. L. E. Visser, R. H. N. van Schaik, M. van Vliet, P. H. Trienekens, P. A. G. M. De Smet, A. G. Vulto, A. Hofman, C. M. van Duijn, B. H. C. Stricker, Clin. Pharmacol. Ther. 2005, 77, 479.
17. F. P. Rowe, C. J. Plant, A. Bradfield, J. Hyg. 1981, 87, 171.
18. V. G. Manolopoulos, G. Ragia, A. Tavridou, J. Pharm. Pharmacol. Pharmacogenomics 2010, 11, 493.
19. W. Schmidt, E. Jahnchen, J. Pharm. Pharmacol. 1977, 29, 266.
20. H. P. Rang, M. M. Dale, J. M. Ritter, P. Gardner, Pharmacology, 4 th ed, Churchill Livingston, Philadephia, 2001
21. H. J. Bardsley, A. K. Daly, WO 00/43003, 2000.
22. For selected reviews, see
23. A. S. Demir, C. Tanyeli, V. Gklbeyaz, H. Akgkn, Turk. J. Chem. 1996, 20, 139
24. A. Robinson, H. Y. Li, J. Feaster, Tetrahedron Lett. 1996, 37, 8321
25. G. Cravotto, G. M. Nano, G. Palmisano, S. Tagliapietra, Tetrahedron: Asymmetry 2001, 12, 707.
26. For book reviews of asymmetric organocatalysis, see
27. A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinhein 2005
28. Enantioselective Organocatalysis (Ed.:, P. I. Dalko,), Wiley-VCH, Weinhein 2007
29. Hydrogen Bonding in Organic Synthesis (Ed.:, P. M. Pihko,), Wiley-VCH, Weinhein 2009.
30. For limited examples, see
31. H. Kim, C. Yin, P. Preston, J. Chin, Org. Lett. 2006, 8, 5239
32. J. W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J. G. Deng, Y. C. Chen, Org. Lett. 2007, 9, 413
33. T. E. Kristensen, K. Vestli, F. K. Hansen, T. Hansen, Eur. J. Org. Chem. 2009, 5185
34. N. Halland, T. Hansen, K. A. Jogensen, Angew. Chem. 2003, 115, 5105
35. Angew. Chem. Int. Ed. 2003, 42, 4955
36. N. Halland, T. Velgarard, K. A. Jørgensen, J. Org. Chem. 2003, 68, 5067.
37. For selected examples of hydrogen-bonding-mediated catalysis, see
38. S.-K. Tian, Y.-G. Chen, J.-F. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621
39. Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299
40. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999
41. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
42. T. Akiyama, J. Itoh, K. Fuchibe, Chem. Rev. 2007, 107, 5744
43. X.-H. Yu, W. Wang, Chem. Asian J. 2008, 3, 516
44. M. D. Pluth, R. G. Bergman, K. N. Raymond, Acc. Chem. Res. 2009, 42, 1650
45. H. Iida, M. J. Krische, Top. Curr. Chem. 2007, 279, 77
46. E. A. Colby Davie, S. M. Mennen, Y. Xu, S. J. Miller, Chem. Rev. 2007, 107, 5759.
47. For selected examples of chiral bifunctional thiourea catalysis, see
48. M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 5315
49. M. S. Sigman, P. Vachal, E. Jacobsen, Angew. Chem. 2000, 112, 1336
50. Angew. Chem. Int. Ed. 2000, 39, 1279
51. P. Vachal, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012
52. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672
53. T. Okino, Y. Hoashi, T. Furukawa, Y. T. X. Xu, J. Am. Chem. Soc. 2005, 127, 119
54. P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289
55. P. M. Pihko, Angew. Chem. 2004, 116
56. Angew. Chem. Int. Ed. 2004, 43, 2062
57. S. J. Connon, Chem. Eur. J. 2006, 12, 5418
58. S. J. Zuend, P. C. Matthew, P. L. Mathieu, E. N. Jacobsen, Nature 2009, 461, 968
59. A. Peschiulli, B. Procuranti, C. J. O'Connor, S. J. Connon, Nat. Chem. 2010, 2, 380
60. S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525
61. Angew. Chem. Int. Ed. 2005, 44, 6367.
62. B. Vakulya, S. Varga, A. Csampai, T. Soós, Org. Lett. 2005, 7, 1967.
63. S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D. P. Curran, J. Am. Chem. Soc. 1998, 120, 12355
64. K. B. Jensen, J. Thorhauge, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2001, 113, 164
65. Angew. Chem. Int. Ed. 2001, 40, 160
66. S. Tardy, A. Tatibout, P. Rollin, G. Dujardin, Synlett 2006, 1425
67. F. Gohier, K. Bouhadjera, D. Faye, C. Gaulon, V. Maisonneuve, G. Dujardin, R. Dhal, Org. Lett. 2007, 9, 211
68. R. P. Herrera, D. Monge, M. Z. Elol'sa, R. Fernandez, J. M. Lassaletta, Org. Lett. 2007, 9, 3303.
69. Our group successful uncovered a series of indene scaffold based amine-thiourea catalysts and applied to catalyze some novel reactions with excellent stereocontrol.
70. CCDC 784873 (3 c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via