Organocatalyzed asymmetric synthesis of dihydrodibenzofurans based on a dienamine process

Organic Letters

Volumn 15, Issue 19, 2013, Pages 4980-4983

  Wang, Zi Yu ^a   Wong, Wing Tak ^a   Yang, Dan ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

BENZOFURANS; CATALYSIS; HYDROGENATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84885119307     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402288y     Document Type: Article

References (35)

1. Mimaki, Y.; Kameyama, A.; Sashida, Y.; Miyata, Y.; Fujii, A. Chem. Pharm. Bull. 1995, 43, 893
2. Portet, B.; Fabre, N.; Roumy, V.; Gornitzka, H.; Bourdy, G.; Chevalley, S.; Sauvain, M.; Valentin, A.; Moulis, C. Phytochemistry 2007, 68, 1312
3. Seephonkai, P.; Popescu, R.; Zehl, M.; Krupitza, G.; Urban, E.; Kopp, B. J. Nat. Prod. 2011, 74, 712
4. Marco Contelles, J.; Carreiras, M. D. C.; Rodriguez, C.; Villarroya, M.; Garcia, A. G. Chem. Rev. 2006, 106, 116
5. Jin, Z. Nat. Prod. Rep. 2003, 20, 606
6. Hoshino, O. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 51, pp 323.
7. Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, pp 252.
8. Chang, J. H.; Kang, H. U.; Jung, I. H.; Cho, C. G. Org. Lett. 2010, 12, 2016
9. Hosokawa, T.; Ohkata, H.; Moritani, I. Bull. Chem. Soc. Jpn. 1975, 48, 1533
10. Hosokawa, T.; Miyagi, S.; Murahashi, S. I.; Sonoda, A. J. Org. Chem. 1978, 43, 2752
11. Richard, C. L.; Norman, B. P.; Kris, N. J. Org. Chem. 1990, 55, 3447
12. Hayashi, T.; Yamasaki, K.; Mimura, M.; Uozumi, Y. J. Am. Chem. Soc. 2004, 126, 3036
13. Nguyen, R. V.; Yao, X. Q.; Li, C. J. Org. Lett. 2006, 8, 2397
14. Grant, V. H.; Liu, B. Tetrahedron Lett. 2005, 46, 1237
15. Liu, Q.; Han, B.; Zhang, W.; Yang, L.; Liu, Z. L.; Yu, W. Synlett 2005, 14, 2248
16. Delgado, J.; Espinós, A.; Jiménez, M. C.; Miranda, M. A. Chem. Commun. 2002, 2636
17. Graham, S. R.; Murphy, J. A.; Coates, D. Tetrahedron Lett. 1999, 40, 2415
18. Bertelsen, S.; Marigo, M.; Brandes, S.; Dinér, P.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 12973
19. Jensen, K. L.; Dickmeiss, G.; Jiang, H.; Albrecht, Ł.; Jørgensen, K. A. Acc. Chem. Res. 2012, 45, 248
20. Nielsen, M.; Worgull, D.; Zweifel, T.; Gschwend, B.; Bertelsen, S.; Jørgensen, K. A. Chem. Commun. 2011, 47, 632
21. Ramachary, D. B.; Reddy, Y. V. Eur. J. Org. Chem. 2012, 865
22. Orue, A.; Reyes, E.; Vicario, J. L.; Carrillo, L.; Uria, U. Org. Lett. 2012, 14, 3740
23. Cassani, C.; Melchiorre, P. Org. Lett. 2012, 14, 5590
24. Hong, B. C.; Wu, M. F.; Tseng, H. C.; Liao, J. H. Org. Lett. 2006, 8, 2217
25. Hong, B. C.; Wu, M. F.; Tseng, H. C.; Huang, G. F.; Su, C. F.; Liao, J. H. J. Org. Chem. 2007, 72, 8459
26. Hong, B. C.; Tseng, H. C.; Chen, S. H. Tetrahedron 2007, 63, 2840
27. Similar work by Watanabe: Bench, B. J.; Liu, C.; Evett, C. R.; Watanabe, C. M. H. J. Org. Chem. 2006, 71, 9458
28. Figueiredo, R. M.; Fröhlich, R.; Christmann, M. Angew. Chem., Int. Ed. 2008, 47, 1450
29. Han, B.; Xiao, Y. C.; He, Z. Q.; Chen, Y. C. Org. Lett. 2009, 11, 4660
30. Han, B.; He, Z. Q.; Li, J. L.; Li, R.; Jiang, K.; Liu, T. Y.; Chen, Y. C. Angew. Chem., Int. Ed. 2009, 48, 5474
31. Li, J. L.; Kang, T. R.; Zhou, S. L.; Li, R.; Wu, L.; Chen, Y. C. Angew. Chem., Int. Ed. 2010, 49, 6418
32. Jia, Z. J.; Zhou, Q.; Zhou, Q. Q.; Chen, P. Q.; Chen, Y. C. Angew. Chem., Int. Ed. 2011, 50, 8638
33. Han, B.; Xiao, Y. C.; Yao, Y.; Chen, Y. C. Angew. Chem., Int. Ed. 2010, 49, 10189
34. Li, J. L.; Zhou, S. L.; Han, B.; Wu, L.; Chen, Y. C. Chem. Commun. 2010, 46, 2665
35. The trans-product has much higher ring strain; see: Gordon, H. L.; Freeman, S.; Hudlicky, T. Synlett 2005, 2911