Rh(I)-catalyzed carbonylative carbocyclization of tethered ene- and yne-cyclopropenes

Organic Letters

Volumn 12, Issue 13, 2010, Pages 3082-3085

  Li, Changkun ^a   Zhang, Hang ^a   Feng, Jiajie ^a   Zhang, Yan ^a   Wang, Jianbo ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; CYCLOPROPANE DERIVATIVE; PHENOL DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOHEXANONES; CYCLOPROPANES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENOLS; RHODIUM; STEREOISOMERISM;

EID: 77954104440     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101091r     Document Type: Article

References (70)

1. Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; Chapter 11, p 215
2. Jeong N., Ed. Chapter 12, p 241
3. Robinson J. E., Ed.); Chapter 13, p 263
4. Wender, P. A.; Gamber, G. G.; Williams, T. J., Ed.).
5. For a recent review on the Pauson-Khand reaction, see
6. Lee, H.-W.; Kwong, F.-Y. Eur. J. Org. Chem. 2010, 789
7. Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249
8. Jeong, N. Organometallics 1998, 17, 3642
9. Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771
10. Croatt, M. P.; Wender, P. A. Eur. J. Org. Chem. 2010, 19 and references cited therein
11. Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876
12. Wang, Y.; Wang, J.; Su, J.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 10060
13. For selected examples of vinylcyclopropane in metal-catalyzed carbocyclization, see
14. Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Pham, S. M.; Zhang, L. J. Am. Chem. Soc. 2005, 127, 2836
15. Wegner, H. A.; de Meijere, A.; Wender, P. A. J. Am. Chem. Soc. 2005, 127, 6530
16. Trost, B. M.; Shen, H. C.; Horne, D. B.; Toste, F. D.; Steinmetz, B. G.; Koradin, C. Chem.-Eur. J. 2005, 11, 2577
17. Wender, P. A.; Haustedt, L. O.; Lim, J.; Love, J. A.; Williams, T. J.; Yoon, J.-Y. J. Am. Chem. Soc. 2006, 128, 6302
18. Kim, S. Y.; Lee, S. I.; Choi, S. Y.; Chung, Y. K. Angew. Chem., Int. Ed. 2008, 47, 4914
19. Jiao, L.; Ye, S.; Yu, Z.-X. J. Am. Chem. Soc. 2008, 130, 7178
20. Jiao, L.; Chen, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2008, 130, 4421
21. Fan, X.; Tang, M.-X.; Zhuo, L.-G.; Tu, Y. Q.; Yu, Z.-X. Tetrahedron Lett. 2009, 50, 155
22. Fan, X.; Zhuo, L.-G.; Tu, Y. Q.; Yu, Z.-X. Tetrahedron 2009, 65, 4709
23. Li, Q.; Jiang, G.-J.; Jiao, L.; Yu, Z.-X. Org. Lett. 2010, 12, 1332
24. Jiao, L.; Lin, M.; Yu, Z.-X. Chem. Commun. 2010, 46, 1059 For selected examples of alkylidencyclopropane as three carbon component in transition metal catalyzed cycloadditions, see:
25. Evans, P. A.; Inglesby, P. A. J. Am. Chem. Soc. 2008, 130, 12838
26. Saito, S.; Masuda, M.; Komagawa, S. J. Am. Chem. Soc. 2004, 126, 10540
27. Koga, Y.; Narasaka, K. Chem. Lett. 1999, 705
28. For recent reviews on cyclopropenes, see
29. Baird, M. S. Chem. Rev. 2003, 103, 1271
30. Walsh, R. Chem. Soc. Rev. 2005, 34, 714
31. Rubin, M.; Rubina, M.; Gevorgyan, V. Synthesis 2006, 1221
32. Fox, J. M.; Yan, N. Curr. Org. Chem. 2005, 9, 719
33. Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295
34. Marek, I.; Simaan, S.; Masarwa, A. Angew. Chem., Int. Ed. 2007, 46, 7364
35. For a review on metal-catalyzed reaction of cyclopropenes, see
36. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
37. For studies on strain energy of cyclopropenes, see
38. Wiberg, K. W.; Fenoglio, R. A. J. Am. Chem. Soc. 1968, 90, 3395
39. Johnson, W. T. G.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 5930
40. Bach, R. D.; Dmitrenko, O. J. Am. Chem. Soc. 2004, 126, 4444
41. Wiberg, K. W. Angew. Chem., Int. Ed. Engl. 1986, 25, 312
42. For a review on the direct insertion of metal into the cyclopropene if bond, see
43. Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241 For an example, see:
44. Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297
45. Cho, S. H.; Liebeskind, L. S. J. Org. Chem. 1987, 52, 2631
46. Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1991, 56, 6971
47. Padwa, A.; Xu, S. L. J. Am. Chem. Soc. 1992, 114, 5881
48. Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642
49. For selected examples of transition-metal-catalyzed ring opening of cyclopropenes, see the following. Rh(II)-catalyzed reaction
50. Cho, S. H.; Liebeskind, L. S. J. Org. Chem. 1987, 52, 2631
51. Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642
52. Müller, P.; Pautex, N.; Doyle, M. P.; Bagheri, V. Helv. Chim. Acta 1990, 73, 1233
53. Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1991, 56, 6971
54. Müller, P.; Gränicher, C. Helv. Chim. Acta 1993, 76, 521
55. Müller, P.; Gränicher, C. Helv. Chim. Acta 1995, 78, 129
56. Chuprakov, S.; Gevorgyan, V. Org. Lett. 2007, 9, 4463 Ag(I)-catalyzed reaction:
57. Padwa, A.; Blacklock, T. J.; Loza, R. J. Am. Chem. Soc. 1981, 103, 2404
58. Padwa, A.; Blacklock, T. J.; Loza, R. J. Org. Chem. 1982, 47, 3712 Mo-catalyzed reaction:
59. Semmelhack, M. F.; Ho, S.; Steigerwald, M.; Lee, M. C. J. Am. Chem. Soc. 1987, 109, 4397
60. Semmelhack, S M. F.; Ho, S.; Cohen, D.; Steigerwald, M.; Lee, M. C.; Lee, G.; Gilbert, A. M.; Wulff, W. D.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7108
61. Pd- or Cu-catalyzed reactions: Ma, S.; Zhang, J. J. Am. Chem. Soc. 2003, 125, 12386
62. Shao, L.-X.; Zhang, Y.-P.; Qi, M.-H.; Shi, M. Org. Lett. 2007, 9, 117
63. Au-catalyzed reaction: Zhu, Z.-B.; Shi, M. Chem.-Eur. J. 2008, 14, 10219
64. Bauer, J. T.; Hadfield, M. S.; Lee, A.-L. Chem. Commun. 2008, 6405
65. Li, C.; Zeng, Y.; Wang, J. Tetrahedron Lett. 2009, 50, 2956
66. Isobe, H.; Sato, S.; Tanaka, T.; Tokuyama, H.; Nakamura, E. Org. Lett. 2004, 6, 3569
67. Wender, P. A.; Paxton, T. J.; Williams, T. J. J. Am. Chem. Soc. 2006, 128, 14814
68. For mechanistic studies on Rh(I)-catalyzed carbonylative carbocyclization, see
69. Yu, Z.-X.; Cheong, P. H.-Y.; Liu, P.; Legault, C. Y.; Wender, P. A.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 2378
70. Wang, H.; Sawyer, J. R.; Evans, P. A.; Baik, M.-H. Angew. Chem., Int. Ed. 2008, 47, 342