Synthesis of cyclic guanidines via Pd-catalyzed alkene carboamination

Organic Letters

Volumn 15, Issue 21, 2013, Pages 5420-5423

  Zavesky, Blane P ^a   Babij, Nicholas R ^a   Fritz, Jonathan A ^a,b   Wolfe, John P ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b AQUINAS COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; GUANIDINE DERIVATIVE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKENES; AMINATION; CATALYSIS; GUANIDINES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84887058416     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402377y     Document Type: Article

References (37)

1. Wei, X.; Henriksen, N. M.; Skalicky, J. J.; Harper, M. K.; Cheatham, T. E., III; Ireland, C. M.; Van Wagoner, R. M. J. Org. Chem. 2011, 76, 5515-5523
2. Cong, H.-J.; Zhang, S.-W; Shen, Y.; Zheng, Y.; Huang, Y.-J.; Wang, W.-Q.; Leng, Y.; Xuan, L.-J. J. Nat. Prod. 2013, 76, 1351-1357
3. Berlinck, R. G. S.; Trindade-Silva, A. E.; Santos, M. F. C. Nat. Prod. Rep. 2012, 29, 1382-1406
4. Berlinck, R. G. S.; Burtoloso, A. C. B.; Trindade-Silva, A. E.; Romminger, S.; Morais, R. P.; Bandeira, K.; Mizuno, C. M. Nat Prod. Rep. 2010, 27, 1871-1907
5. Berlinck, R. G. S.; Burtoloso, A. C. B.; Kossuga, M. H. Nat. Prod. Rep. 2008, 25, 919-954
6. Hensler, M. E.; Bernstein, G.; Nizet, V.; Nefzi, A. Bioorg. Med. Chem. Lett. 2006, 16, 5073-5079
7. Nefzi, A.; Appel, J.; Arutyunyan, S.; Houghten, R. A. Bioorg. Med. Chem. Lett. 2009, 19, 5169-5175
8. Rideout, M. C.; Boldt, J. L.; Vahi-Ferguson, G.; Salamon, P.; Nefzi, A.; Ostresh, J. M.; Giulianotti, M.; Pinilla, C.; Segall, A. M. Mol. Divers. 2011, 15, 989-1005
9. For a review, see: Selig, P. Synthesis 2013, 45, 703-718
10. O'Donovan, D. H.; Rozas, I. Tetrahedron Lett. 2012, 53, 4532-4535
11. Kim, H.-O.; Mathew, F.; Ogbu, C. Synlett 1999, 193-194
12. Nalli, S. M.; Clarkson, G. J.; Franklin, A. S.; Bellone, G.; Shipman, M. Synlett 2008, 2339-2341
13. Huber, D.; Leclerc, G.; Ehrhardt, J. D.; Andermann, G. Tetrahedron Lett. 1987, 28, 6453-6456
14. Hövelmann, C. H.; Streuff, J.; Brelot, L.; Muñiz, K. Chem. Commun. 2008, 2334-2336
15. Zhao, B.; Du, H.; Shi, Y. Org. Lett. 2008, 10, 1087-1090
16. Kim, M.; Mulcahy, J. V.; Espino, C. G.; Du Bois, J. Org. Lett. 2006, 8, 1073-1076
17. Bhonde, V. R.; Looper, R. E. J. Am. Chem. Soc. 2011, 133, 20172-20174
18. Gibbons, J. B.; Gligorich, K. M.; Welm, B. E.; Looper, R. E. Org. Lett. 2012, 14, 4734-4737
19. Giles, R. L.; Sullivan, J. D.; Steiner, A. M.; Looper, R. E. Angew. Chem., Int. Ed. 2009, 48, 3116-3120
20. Mulcahy, J. V.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 12630-12631
21. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890
22. Büchi, G.; Rodriguez, A. D.; Yakushijin, K. J. Org. Chem. 1989, 54, 4494-4496
23. Wolfe, J. P. Eur. J. Org. Chem. 2007, 571-582
24. Wolfe, J. P. Synlett 2008, 2913-2937
25. Schultz, D. M.; Wolfe, J. P. Synthesis 2012, 44, 351-361
26. Yong, Y. F.; Kowalski, J. A.; Lipton, M. A. J. Org. Chem. 1997, 62, 1540-1542
27. Li, D.; Guang, J.; Zhang, W.-X.; Wang, Y.; Xi, Z. Org. Biomol. Chem. 2010, 8, 1816-1820
28. Bailey, P. J.; Pace, S. Coord. Chem. Rev. 2001, 214, 91-141
29. Rauws, T. R. M.; Maes, B. U. W. Chem. Soc. Rev. 2012, 41, 2463-2497
30. Fritz, J. A.; Wolfe, J. P. Tetrahedron 2008, 64, 6838-6852
31. Fritz, J. A.; Nakhla, J. S.; Wolfe, J. P. Org. Lett. 2006, 8, 2531-2534
32. Babij, N. R.; Wolfe, J. P. Angew. Chem., Int. Ed. 2012, 51, 4128-4130
33. Babij, N. R.; Wolfe, J. P. Angew. Chem., Int. Ed. 2013, 52, 9247-9250
34. Neukom, J. D.; Perch, N. S.; Wolfe, J. P. J. Am. Chem. Soc. 2010, 132, 6276-6277
35. Hanley, P. S.; Markovic, D.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 6302-6303
36. Hopkins, B. A.; Wolfe, J. P. Angew. Chem., Int. Ed. 2012, 51, 9886-9890
37. Mai, D. N.; Wolfe, J. P. J. Am. Chem. Soc. 2010, 132, 12157-12159