Synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones

Organic Letters

Volumn 15, Issue 18, 2013, Pages 4634-4637

  Zhuo, Lian Gang ^a   Yao, Zhong Ke ^a   Yu, Zhi Xiang ^a  

^a Peking University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84884577711     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401607c     Document Type: Article

References (53)

1. Larock, R. C. Comprehensive organic transformations: a guide to functional group preparations, 2 nd ed.; Wiley-VCH: New York, 1999.
2. Uma, R.; Crévisy, C.; Grée, R. Chem. Rev. 2003, 103, 27
3. Bouziane, A.; Carboni, B.; Bruneau, C.; Carreaux, F.; Renaud, J. Tetrahedron 2008, 64, 11745
4. Krompiec, S.; Krompiec, M.; Penczek, R.; Ignasiak, H. Coord. Chem. Rev. 2008, 252, 1819
5. Kuznik, N.; Krompiec, S. Coord. Chem. Rev. 2007, 251, 222
6. Fe, Rh, and Ru, see: Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139
7. Ohmura, T.; Shirai, Y.; Yamamoto, Y.; Miyaura, N. Chem. Commun. 1998, 1337
8. Ohmura, T.; Yamamoto, Y.; Miyaura, N. Organometallics 1999, 18, 413
9. Yamamoto, Y.; Miyairi, T.; Ohmura, T.; Miyaura, N. J. Org. Chem. 1999, 64, 296
10. Wille, A.; Tomm, S.; Frauenrath, H. Synthesis 1998, 305
11. Sharma, S. K.; Srivastava, V. K.; Jasra, R. V. J. Mol. Catal. A: Chem. 2006, 245, 200
12. Jinesh, C. M.; Antonyrai, C. A.; Kannan, S. Catal. Today 2009, 141, 176
13. Lim, H. J.; Smith, C. R.; RajanBabu, T. V. J. Org. Chem. 2009, 74, 4565
14. Wang, L.; Liu, Z.; Bai, R.; Pan, Y.; Lei, A. Chem. Commun. 2013, 49, 7923
15. Pd, see: Gautheir, D.; Lindhardt, A. T.; Olsen, E. P. K.; Overgaard, J.; Skrydstrup, T. J. Am. Chem. Soc. 2010, 132, 7998
16. Pt, see: Scarso, A.; Colladon, M.; Sgarbossa, P.; Michelin, R. A.; Strukul, G. Organometallics 2010, 29, 1487
17. Tani, K.; Yamagata, T.; Akutagawa, S.; Kumobayashi, H.; Taketomi, T.; Takaya, H.; Miyashita, A.; Noyori, R.; Otsuka, S. J. Am. Chem. Soc. 1984, 106, 5208
18. Alphonse, F. A.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, 11754
19. Tsang, D. S.; Yang, S.; Alphonse, F. A.; Yudin, A. K. Chem.-Eur. J. 2008, 14, 886
20. Suzuki, H.; Koyama, Y.; Moro-Oka, Y.; Ikawa, T. Tetrahedron Lett. 1979, 20, 1415
21. Wipf, P.; Spencer, S. R. J. Am. Chem. Soc. 2005, 127, 225
22. Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.; Nishida, A. J. Org. Chem. 2006, 71, 4255
23. Hanessian, S.; Giroux, S.; Larrson, A. Org. Lett. 2006, 8, 5481
24. Grotjahn, D. B.; Larsen, C. R.; Gustafson, J. L.; Nair, R.; Sharma, A. J. Am. Chem. Soc. 2007, 129, 9592
25. Sivaramakrishna, A.; Mushonga, P.; Rogers, I. L.; Zheng, F.; Haines, R. J.; Nordlander, E.; Moss, J. R. Polyhedron 2008, 27, 1911
26. Donohoe, T. J.; O'Riordan, T. J. C.; Rosa, C. P. Angew. Chem., Int. Ed. 2009, 48, 1014
27. Grotjahn, D. B.; Larsen, C. R.; Erdogan, G.; Gustafson, J. L.; Sharma, A.; Nair, R. Catal. Org. React. 2009, 123, 379
28. Larsen, C. R.; Grotjahn, D. B. J. Am. Chem. Soc. 2012, 134, 10357
29. For a recent review focusing on the synthesis of Z -alkenes, see: Oger, C.; Balas, L.; Durand, T.; Galano, J.-M. Chem. Rev. 2012, 113, 1313
30. La Pierre, H. S.; Arnold, J.; Toste, F. D. Angew. Chem., Int. Ed. 2011, 50, 3900
31. Li, J.; Hua, R. Chem.-Eur. J. 2011, 17, 8462
32. Reyes-Sánchez, A. n.; Cañavera-Buelvas, F.; Barrios-Francisco, R.; Cifuentes-Vaca, O. L.; Flores-Alamo, M.; García, J. J. Organometallics 2011, 30, 3340
33. Shen, R.; Chen, T.; Zhao, Y.; Qiu, R.; Zhou, Y.; Yin, S.; Wang, X.; Goto, M.; Han, L.-B. J. Am. Chem. Soc. 2011, 133, 17037
34. Smitrovich, J. H.; Woerpel, K. A. J. Am. Chem. Soc. 1998, 120, 12998
35. Trost, B. M.; Heinemann, C.; Ariza, X.; Weigand, S. J. Am. Chem. Soc. 1999, 121, 8667
36. Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 2000, 65, 1601
37. Ely, R. J.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 2534
38. Bohn, M. A.; Schmidt, A.; Hilt, G.; Dindaroglu, M.; Schmalz, H. G. Angew. Chem., Int. Ed. 2011, 50, 9689
39. Giannerini, M.; Fananas-Mastral, M.; Feringa, B. L. J. Am. Chem. Soc. 2012, 134, 4108
40. Ibrahem, I.; Yu, M.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3844
41. Meek, S. J.; O'Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature 2011, 471, 461
42. Wang, Y.; Jimenez, M.; Hansen, A. S.; Raiber, E.; Schreiber, S. L.; Young, D. W. J. Am. Chem. Soc. 2011, 133, 9196
43. Rosebrugh, L. E.; Herbert, M. B.; Marx, V. M.; Keitz, B. K.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 1276
44. Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Sythesis: Background and Detailed Mechanisms; Elsevier: Amsterdam, 2005. For selected recent examples, see
45. Ando, K.; Okumura, M.; Nagaya, S. Tetrahedron Lett. 2013, 54, 2026
46. Hodgson, D. M.; Arif, T. Chem. Commun. 2011, 47, 2685
47. Dong, D.-J.; Li, H.-H.; Tian, S.-K. J. Am. Chem. Soc. 2010, 132, 5018
48. Punner, F.; Schmidt, A.; Hilt, G. Angew. Chem., Int. Ed. 2012, 51, 1270
49. Wang, Z.; Chen, Z. L.; Bai, S.; Li, W.; Liu, X. H.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2012, 51, 2776
50. Egi, M.; Umemura, M.; Kawai, T.; Akai, S. Angew. Chem., Int. Ed. 2011, 50, 12197
51. Wang, D.; Ye, X.; Shi, X. Org. Lett. 2010, 12, 2088
52. Al-Masum, M.; Liu, K. Y. Tetrahedron Lett. 2011, 52, 5090
53. 2-catalyzed olefin isomerization was also found in diene isomerization; see: Yao, Z.-K.; Li, J.; Yu, Z.-X. Org. Lett. 2011, 13, 134