Iridium-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadienes with amine nucleophiles

Organometallics

Volumn 29, Issue 16, 2010, Pages 3477-3480

  Yang, Dingqiao ^a   Long, Yuhua ^a   Zhang, Junfang ^a   Zeng, Heping ^a   Wang, Sanyong ^b   Li, Chunrong ^b  

^a SOUTH CHINA NORMAL UNIVERSITY   (China)

^b Guangdong Food Industry Institute   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC RINGS; PRIMARY AROMATIC AMINES; RING OPENING REACTION; TRANS CONFIGURATION;

CATALYSIS; ENANTIOSELECTIVITY; NUCLEOPHILES; ORGANIC COMPOUNDS; X RAY CRYSTALLOGRAPHY;

IRIDIUM;

EID: 77955687867     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100384q     Document Type: Article

References (48)

1. For examples, see: Nomura, N.; Komiyama, S.; Kasugai, H.; Saba, M. J. Am. Chem. Soc. 2008, 130, 812-814
2. Alexakis, A.; Hajjaji, S. E.; Polet, D.; Rathgeb, X. Org. Lett. 2007, 9, 3393-3395
3. Polet, D.; Alexakis., A. Org. Lett. 2005, 7, 1621-1624
4. Kanayama, T.; Yoshida, K.; Miyabe, H.; Kimachi, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6197-6201
5. Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 5560-5562
6. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844
7. Johnson, B. M.; Chang, P. T. L. Anal. Profiles Drug Subst. Excipients 1996, 24, 443
8. Snyder, S. E. J. Med. Chem. 1995, 38, 2395-2409
9. Kamal, A.; Gayatri, L. Tetrahedron 1996, 37, 3359-3362
10. Kim, K.; Guo, Y.; Sulikowski, G. A. J. Org. Chem. 1995, 60, 6866-6871
11. Perrone, R. J. Med. Chem. 1995, 38, 942-949
12. Nishimura, T.; Tsurumaki, E.; Kawamoto, T.; Guo, X. X.; Hayashi, T. Org. Lett. 2008, 10, 4057-4060
13. Nakamura, M.; Matsuo, K.; Inlue, T.; Nakamura, E. Org. Lett. 2003, 5, 1373-1375
14. Caple, R.; Chen, G. M. S.; Neison, J. D. J. Org. Chem. 1971, 36, 2874-2876
15. Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803-2806
16. Lautens, M. Synlett 1993, 177-185
17. Lautens, M.; Colucci, J. T.; Hiebert, S.; Smith, N. D.; Bouchain, G. Org. Lett. 2002, 4, 1879-1882
18. Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48-58
19. Lautens, M.; Fagnou, K.; Taylor, M. Org. Lett. 2000, 2, 1677-1679
20. Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311-1314
21. Lautens, M.; Hiebert, S.; Renaud, J. L. Org. Lett. 2000, 2, 1971-1973
22. Lautens, M.; Renaud, J. L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804-1805
23. Lautens, M.; Fagnou, K. Tetrahedron 2001, 57, 5067-5072
24. Lautens, M.; Leong, P. J. Org. Chem. 2004, 69, 2194-2196
25. Lautens, M.; Fagnou, K.; Yang, D. Q. J. Am. Chem. Soc. 2003, 125, 14884-14892
26. Lautens, M.; Fagnou, K. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5455-5460
27. Lautens, M.; McManus, H. A.; Fleming, M. J. Angew. Chem., Int. Ed. 2007, 46, 433-436
28. Zhang, T. K.; Mo, D. L.; Dai, L. X.; Hou, X. L. Org. Lett. 2008, 10, 3689-3692
29. Li, M.; Yan, X. X.; Hong, W.; Zhu, X. Z.; Cao, B. X.; Sun, J.; Hou, X. L. Org. Lett. 2004, 6, 2833-2835
30. Wu, M. S.; Rayabarapu, D. K.; Cheng, C. H. J. Org. Chem. 2004, 69, 8407-8412
31. Feng, C. C.; Nandi, M.; Sambaiah, T.; Cheng, C. H. J. Org. Chem. 1999, 64, 3538-3543
32. Li, L. P.; Rayabarapu, D. K.; Nandi, M.; Cheng, C. H. Org. Lett. 2003, 5, 1621-1624
33. Lopez, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2004, 126, 12784-12785
34. Lopez, F.; Van Zijl, A. W.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2006, 409-411
35. Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426-2428
36. Falciola, C. A.; Tissot-Croset, K.; Alexakis, A. Angew. Chem., Int. Ed. 2006, 45, 5995-5998
37. Lautens, M.; Dockendorff, C. Org. Lett. 2003, 5, 3695-3698
38. Chen, C. L.; Martin, S. F. J. Org. Chem. 2006, 71, 4810-4817
39. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978-979
40. Nakamura, M.; Matsuo, K.; Inoue, T.; Nakamura, E. Org. Lett. 2003, 5, 1373-1375
41. Villeneuve, K.; Tam, W. J. Am. Chem. Soc. 2006, 128, 3514-3515
42. Cho, Y. H.; Zunic, V.; Senboku, H.; Olsen, M.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 6837-6846
43. Cho, Y. H.; Fayol, A.; Lautens, M. Tetrahedron: Asymmetry 2006, 17, 416-427
44. Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532-533
45. Lautens, M.; Ma, S. J. Org. Chem. 1996, 61, 7246-7247
46. Lautens, M.; Rovis, T. J. Org. Chem. 1997, 62, 5246-5247
47. Yang, D. Q.; Long, Y. H.; Wang, H.; Zhang, Z. M. Org. Lett. 2008, 10, 4723-4726
48. Yang, D. Q.; Hu, P.; Long, Y. H.; Wu, Y. J.; Zeng, H. P.; Wang, H.; Zuo, X. J. Beilstein J. Org. Chem. 2009, 5, No. 53.