Rhodium-catalyzed regioselective amination of secondary allylic trichloroacetimidates with unactivated aromatic amines

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4580-4583

  Arnold, Jeffrey S ^a   Stone, Robert F ^a   Nguyen, Hien M ^a  

^a The University of Iowa   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DRUG DERIVATIVE; RHODIUM; TRICHLOROACETAMIDE; TRICHLOROACETIC ACID;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

AMINATION; AMINES; CATALYSIS; MOLECULAR STRUCTURE; RHODIUM; TRICHLOROACETIC ACID;

EID: 77957825233     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1019025     Document Type: Article

References (35)

1. Glasby, J. S. Encyclopedia of the Alkaloids; Plenum: New York, NY, 1975; Vol. 1 - 5.
2. Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689
3. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921
4. Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269
5. Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797
6. Dubovyk, I.; Watson, I. D. G.; Yudin, A. K. J. Am. Chem. Soc. 2007, 129, 14172
7. Takeuchi, R.; Ue, N.; Tanabe, I.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525
8. Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761
9. Mercer, G. J.; Yang, J.; McKay, M. J.; Nguyen, H. M. J. Am. Chem. Soc. 2008, 130, 11210
10. Yang, J.; Cooper-Vanosdell, C.; Mensah, E. A.; Nguyen, H. M. J. Org. Chem. 2008, 73, 794
11. Mensah, E. A.; Nguyen, H. M. J. Am. Chem. Soc. 2009, 131, 8778
12. Fagnou, K.; Lautens, M. Org. Lett. 2000, 2, 2319
13. Overman, L. E. J. Am. Chem. Soc. 1974, 96, 597
14. For a comprehensive review, see
15. Overaman, L. E.; Carpenter, N. E. In Organic Reactions; Overman, L. E., Ed.; Wiley-VCH: Weiheim, 2005; Vol. 66, pp 1 - 107.
16. Tolman, C. A. Chem. Rev. 1977, 77, 313
17. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21
18. Schmidt, R. R.; Jung, K.-H. Carbohydr. Chem. Biochem. 2000, 5
19. Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 1900
20. Schmidt, R. R.; Michel, J. J. Carbohydr. Chem. 1985, 4, 141
21. Zimmermann, P.; Bommer, R.; Bär, T.; Schmidt, R. R. J. Carbohydr. Chem. 1988, 7, 435
22. Schmidt, R. R.; Behrendt, M.; Toepfer, A. Synlett 1990, 694
23. Paulsen, H.; Wilkens, R.; Reck, F.; Brockhausen, I. Liebigs. Ann. Chem. 1992, 1303
24. Kulkarni, S. S.; Hung, S.-C. Lett. Org. Chem. 2005, 2, 670
25. Haase, W. C.; Seeberger, P. H. Curr. Org. Chem. 2000, 4, 481
26. Dobarro-Rodriguez, A.; Trumtel, M.; Wessel, H. P. J. Carbohydr. Chem. 1992, 11, 255
27. 2, and the linear product was obtained as the major isomer.
28. 3.
29. Davoille, R. J.; Rutherford, D. T.; Christie, S. D. R. Tetrahedron. Lett. 2000, 41, 1225
30. Trost, B, M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730
31. Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469
32. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc. 1990, 112, 9590
33. Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647
34. Stanley, L. M.; Bai, C.; Ueda, M.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 8918
35. Trost, B. M.; Fraisse, P. L.; Ball, Z. T. Angew. Chem., Int. Ed. 2002, 41, 1059