Gold(1)-catalyzed intramolecular dihydroamination of allenes with N,N′-disubstituted ureas to form bicyclic imidazolidin-2-ones

Organic Letters

Volumn 11, Issue 12, 2009, Pages 2671-2674

  Li, Hao ^a   Widenhoefer, Ross A ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; FUSED HETEROCYCLIC RINGS; GOLD; IMIDAZOLIDINE DERIVATIVE; UREA;

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

ALKADIENES; AMINATION; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; CYCLIZATION; GOLD; IMIDAZOLIDINES; MOLECULAR STRUCTURE; STEREOISOMERISM; UREA;

EID: 67149095011     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900730w     Document Type: Article

References (45)

1. Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
2. For examples of biologically active imidazolidin-2-ones, see: (a) Li, J.; Sutton, J.; Nirschl, A.; Zou, Y.; Wang, H.; Sun, C.; Pi, Z.; Johnson, R.; Krystek, S.; Seethala, R.; Golla, R.; Sleph, P.; Beehler, B.; Grover, G.; Fura, A.; Vyas, V.; Li, C.; Gougoutas, J.; Galella, M.; Zahler, R.; Ostrowski, J.; Hamann, L. J. Med. Chem. 2007, 50, 3015
3. (b) Salituro, F. G.; Baker, C. T.; Court, J. J.; Deininger, D. D.; Kim, E. E.; Li, B.; Novak, P. M.; Rao, B. G.; Pazhanisamy, S.; Porter, M. D.; Schairer, W. C.; Tung, R. D. Bioorg. Med. Chem. Lett. 1998, 8, 3637
4. (c) Spaltenstein, A.; Almond, M. R.; Bock, W. J.; Cleary, D. G.; Furflne, E. S.; Hazen, R. J.; Kazmierski, W. M.; Salituro, F. G.; Tung, R. D.; Wright, L. L. Bioorg. Med. Chem. Lett. 2000, 10, 1159
5. (d) Kazmierski, W. M.; Furfine, E.; Gray-Nunez, Y.; Spaltenstein, A.; Wright, L. Bioorg. Med. Chem. Lett. 2004, 14, 5685
6. (e) Heidempergher, F.; Pillan, A.; Pinciroli, V.; Vaghi, F.; Arrigoni, C.; Bolis, G.; Caccia, C.; Dho, L.; McArthur, R.; Varasi, M. J. Med. Chem. 1997, 40, 3369
7. (f) Reichard, G. A.; Stengone, C.; Paliwal, S.; Mergelsberg, I.; Majmundar, S.; Wang, C.; Tiberi, R.; McPhail, A. T.; Piwinkski, J. J.; Shih, N.-Y. Org. Lett. 2003, 5, 4249
8. (g) Shue, H. J.; Chen, X.; Shih, N.-Y.; Blythin, D. J.; Paliwal, S.; Lin, L.; Gu, D.; Schwerdt, J. H.; Shah, S.; Reichard, G. A.; Piwinski, J. J.; Duffy, R. A.; Lachowicz, J. E.; Coffin, V. L.; Liu, F.; Nomeir, A. A.; Morgan, C. A.; Varty, G. B. Bioorg. Med. Chem. Lett. 2005, 15, 3896
9. (h) Shue, H.-J.; Chen, X.; Schwerdt, J. H.; Paliwal, S.; Blythin, D. J.; Lin, L.; Gu, D.; Wang, C., Reichard, G. A.; Wang, H.; Piwinski, J. J.; Duffy, R. A.; Lachowicz, J. E.; Coffin, V. L.; Nomeir, A. A.; Morgan, C. A.; Varty, G. B.; Shih, N.-Y. Bioorg. Med. Chem. Lett. 2006, 16, 1065.
10. For early approaches to alkene dihydroamination that employ a stoichiometric amount of transition metal or heavy metal salt, see: (a) Backvall, J.-E. Tetrahedron Lett. 1978, 19, 163
11. (b) Aranda, V. G.; Barluenga, J.; Aznar, F. Synthesis 1974, 504
12. (c) Barluenga, J.; Aznar, F.; de Mattos, M. C. S.; Kover, W. B.; Garcia-Granda, S.; Péiez-Carreño, E. J. Org. Chem. 1991, 56, 2930
13. (d) Chong, A. O.; Oshima, K.; Shaipless, K. B. J. Am. Chem. Soc. 1977, 99, 3420
14. (e) Becker, P. N.; White, M. A.; Bergman, R. G. J. Am. Chem. Soc. 1980, 102, 5676.
15. de Figueiredo, R. M. Angew. Chem., Int. Ed. 2009, 48, 1190.
16. Cochran, B. M.; Michael, F. E. Org. Lett. 2008, 10, 5039.
17. (a) Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250
18. (b) Zawaba, T. P.; Chelmer, S. R. Org. Lett. 2007, 9, 2035.
19. Bar, G. L. J.; Lloyd-Jones, G. C: Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308.
20. (a) Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muniz, K. J. Am. Chem. Soc. 2005, 127, 14586
21. (b) Muñiz, K.; Hovelmann, C. H.; Campos-Gómez, E.; Barluenga, J.; González, J. M.; Streuff, J.; Nieger, M. Chem. Asian J. 2008, 3, 116
22. (c) Muñiz. K.; Hövelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763
23. (d) Muñiz, K.; Streuff, J.; Chávez, P.; Hövelmann, C. H. Chem. Asian J. 2008, 3, 1248
24. (e) Muñiz, K. J. AM. Chem. Soc. 2007, 129, 14542
25. (f) Hövelmann, C. H.; Streuff, J.; Brelot, L.; Muniz, K. Chem. Commun 2008, 2334.
26. Muñiz, K.; Streuff, J.; Hövelmann, C. H.; Núñez. A. Angew. Chem., Int. Ed. 2007, 46, 7125.
27. (a) Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762
28. (b) Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 11688
29. (c) Xu, L.; Du, H.; Shi, Y. J. Org. Chem. 2007, 72, 7038
30. (d) Xu, L.; Shi, Y. J. Org. Chem. 2008, 73, 749.
31. Zhao, B.; Du, H.; Shi, Y. Org. Lett. 2008, 10, 1087.
32. Zhang, Z.; Liu, C.; Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066.
33. (a) Han, X.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2006, 45, 1747
34. (b) Bender, C. R.; Widenhoefer, R. A. Org. Lett. 2006, 8, 5303
35. (c) Bender, C. R.; Widenhoefer, R. A. Chem. Commun. 2006, 4143.
36. 2 for 16 h led to quantitive formation of 9 (see the Supporting Information).
37. 6 (see the Supporting Information).
38. (a) Zhang, Z.; Liu, C., Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066
39. (b) Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2008, 10, 2079
40. (c) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526
41. (d) Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798
42. (e) Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391
43. (f) Liu, Y.; Song, R.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409
44. (g) Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798.
45. Kovacs, G.; Ujaque, G.; Lledos, A. J. Am. Chem. Soc. 2008, 130, 853.