Catalytic asymmetric conjugate allylation of coumarins

Organic Letters

Volumn 13, Issue 15, 2011, Pages 3814-3817

  Kuang, Yulong ^a   Liu, Xiaohua ^a   Chang, Lu ^a   Wang, Min ^a   Lin, Lili ^a   Feng, Xiaoming ^a  

^a Sichuan University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79961098788     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201312y     Document Type: Article

References (58)

1. For selected application of catalytic asymmetric allylation in natural product syntheses, see: de Fátima, Â.; Kohn, L. K.; Antônio, M. A.; de Carvalho, J. E.; Pilli, R. A. Bioorg. Med. Chem. 2005, 13, 2927
2. Sanchez, C. C.; Keck, G. E. Org. Lett. 2005, 7, 3053
3. Itoh, T.; Miyazaki, M.; Fukuoka, H.; Nagata, K.; Ohsawa, A. Org. Lett. 2006, 8, 1295
4. Miyazaki, M.; Ando, N.; Sugai, K.; Seito, Y.; Fukuoka, H.; Kanemitsu, T.; Nagata, K.; Odanaka, Y.; Nakamura, K. T.; Itoh, T. J. Org. Chem. 2011, 76, 534
5. For selected examples of catalytic asymmetric allylation, see: Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799
6. Lu, J.; Ji, S. J.; Teo, Y. C.; Loh, T. P. Org. Lett. 2005, 7, 159
7. Kiyohara, H.; Nakamura, Y.; Matsubara, R.; Kobayashia, S. Angew. Chem., Int. Ed. 2006, 45, 1615
8. Wooten, A. J.; Kim, J. G.; Walsh, P. J. Org. Lett. 2007, 9, 381
9. Massa, A.; Acocella, M. R.; De Sio, V.; Villano, R.; Scettri, A. Tetrahedron: Asymmetry 2009, 20, 202
10. Shi, S. L.; Xu, L. W.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 6638
11. Chakrabarti, A.; Konishi, H.; Yamaguchi, M.; Schneider, U.; Kobayashi, S. Angew. Chem., Int. Ed. 2010, 49, 1838
12. Boyd, D. R.; Sharma, N. D.; Sbircea, L.; Murphy, D.; Malone, J. F.; James, S. L.; Allen, C. C. R.; Hamilton, J. T. G. Org. Biomol. Chem. 2010, 8, 1081
13. Li, J.; Lutz, M.; Spek, A. L.; van Klink, G. P. M.; van Koten, G.; Klein Gebbink, R. J. M. Organometallics 2010, 29, 1379
14. Qiao, X. C.; Zhu, S. F.; Chen, W. Q.; Zhou, Q. L. Tetrahedron: Asymmetry 2010, 21, 1216
15. Wu, Q. F.; He, H.; Liu, W. B.; You, S. L. J. Am. Chem. Soc. 2010, 132, 11418
16. Zhu, S. F.; Qiao, X. C.; Zhang, Y. Z.; Wang, L. X.; Zhou, Q. L. Chem. Sci. 2011, 2, 1135
17. For the character of nucleophiles to Michael reaction, see: Poon, T. J. Chem. Educ. 2002, 79, 264
18. For the studies of character of allyl anion, see: Brickhouse, M. D.; Squires, R. R. J. Am. Chem. Soc. 1988, 110, 2706
19. Linares, M.; Humbel, S.; Braïda, B. J. Phys. Chem. A 2008, 112, 13249
20. Sieber, J. D.; Liu, S.; Morken, J. P. J. Am. Chem. Soc. 2007, 129, 2214
21. Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2008, 130, 4978
22. Brozek, L. A.; Sieber, J. D.; Morken, J. P. Org. Lett. 2011, 13, 995
23. Shizuka, M.; Snapper, M. L. Angew. Chem., Int. Ed. 2008, 47, 5049
24. For the precedent example of generating active organometallic agents from organotin through transmetalation in a conjugate allylation reaction, see: Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389
25. For the biological and pharmaceutical activity of coumarins, see: Takechi, M.; Tanaka, Y.; Takehara, M.; Nonaka, G. I.; Nishioka, I. Phytochemistry 1985, 24, 2245
26. Iinuma, M.; Tanaka, T.; Mizuno, M.; Katsuzaki, T.; Ogawa, H. Chem. Pharm. Bull. 1989, 37, 1813
27. Iinuma, M.; Ohyama, M.; Tanaka, T.; Mizuno, M.; Hong, S. K. Phytochemistry 1991, 30, 3153
28. Vilain, A. C.; Okochi, V.; Vergely, I.; Reboud-Ravaux, M.; Mazaleyrat, J. P.; Wakselman, M. Biochim. Biophys. Acta 1991, 1076, 401
29. Chang, Y. C.; Nair, M. G. J. Nat. Prod. 1995, 58, 1901
30. Hoult, J. R. S.; Payá, M. Gen. Pharmacol. 1996, 27, 713
31. Boyle, F. T.; Costello, G. F. Chem. Soc. Rev. 1998, 27, 251
32. Tillekeratne, L. M. V.; Sherette, A.; Grossman, P.; Hupe, L.; Hupe, D.; Hudson, R. A. Bioorg. Med. Chem. Lett. 2001, 11, 2763
33. Bailly, C.; Bal, C.; Barbier, P.; Combes, S.; Finet, J. P.; Hildebrand, M. P.; Peyrot, V.; Wattez, N. J. Med. Chem. 2003, 46, 5437
34. Roelens, F.; Huvaere, K.; Dhooge, W.; Van Cleemput, M.; Comhaire, F.; De Keukeleire, D. Eur. J. Med. Chem. 2005, 40, 1042
35. Kumar, A.; Singh, B. K.; Tyagi, R.; Jain, S. K.; Sharma, S. K.; Prasad, A. K.; Raj, H. G.; Rastogi, R. C.; Watterson, A. C.; Parmar, V. S. Bioorg. Med. Chem. 2005, 13, 4300
36. Menasria, F.; Azebaze, A. G. B.; Billard, C.; Faussat, A. M.; Nkengfack, A. E.; Meyer, M.; Kolb, J. P. Leuk. Res. 2008, 32, 1914
37. For examples of allylbromide/zinc in an allylation reaction, see: Li, H.; Cheng, H. S.; Seow, A. H.; Loh, T. P. Tetrahedron Lett. 2007, 48, 2209
38. Kong, W.; Fu, C.; Ma, S. Org. Biomol. Chem. 2008, 6, 4587
39. For selected examples of allyltrimethylsilane as the nucleophilic reagent in a conjugate allylation reaction, see: Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673
40. Majetich, G.; Casares, A.; Chapman, D.; Behnke, M. J. Org. Chem. 1986, 51, 1745
41. Hayashi, M.; Mukaiyama, T. Chem. Lett. 1987, 289
42. Lee, P. H.; Lee, K.; Sung, S.; Chang, Y.; S. J. Org. Chem. 2001, 66, 8646
43. For N,N ′-dioxide in an asymmetric allylation reaction of carbonyl, see: Zhang, X.; Chen, D. H.; Liu, X. H.; Feng, X. M. J. Org. Chem. 2007, 72, 5227
44. Zheng, K.; Qin, B.; Liu, X. H.; Feng, X. M. J. Org. Chem. 2007, 72, 8478
45. Huang, J. L.; Wang, J.; Chen, X. H.; Wen, Y. H.; Liu, X. H.; Feng, X. M. Adv. Synth. Catal. 2008, 350, 287
46. For selected examples of N,N ′-dioxide-metal complexes in nucleophilic addition reactions, see: Xie, M. S.; Chen, X. H.; Zhu, Y.; Gao, B.; Lin, L. L.; Liu, X. H.; Feng, X. M. Angew. Chem., Int. Ed. 2010, 49, 3799
47. Cai, Y. F.; Liu, X. H.; Hui, Y. H.; Jiang, J.; Wang, W. T.; Chen, W. L.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2010, 49, 6160
48. Chang, L.; Kuang, Y. L.; Qin, B.; Zhou, X.; Liu, X. H.; Lin, L. L.; Feng, X. M. Org. Lett. 2010, 12, 2214
49. Li, W.; Wang, J.; Hu, X. L.; Shen, K.; Wang, W. T.; Chu, Y. Y.; Lin, L. L.; Liu, X. H.; Feng, X. M. J. Am. Chem. Soc. 2010, 132, 8532
50. Wang, W. T.; Liu, X. H.; Cao, W. D.; Wang, J.; Lin, L. L.; Feng, X. M. Chem.-Eur. J. 2010, 16, 1664
51. Wang, W. T.; Liu, X. H.; Cao, W. D.; Wang, J.; Lin, L. L.; Feng, X. M. Chem.-Eur. J. 2010, 16, 1664
52. Zheng, K.; Yin, C. K.; Liu, X. H.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2011, 50, 2573
53. For primary studies of the copper effect of organotin, see: Han, X.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600
54. Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132
55. CCDC822331 (1a) contains the supplementary crystallographic data for this paper. These data can be obtained free from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-requst/cif.
56. Mori, S.; Nakamura, E. Morden Organocopper Chemistry; Wiley: 2002; Vol. 10, pp 315-346.
57. Biddle, M. M.; Lin, M.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 3830
58. Liu, X.; Lu, Y. Org. Lett. 2010, 12, 5592