Rhi-catalyzed two-component [(5+2)+1] cycloaddition approach toward [5-8-5] ring systems

Chemistry - An Asian Journal

Volumn 5, Issue 7, 2010, Pages 1555-1559

  Huang, Feng ^a   Yao, Zhong Ke ^a   Wang, Yi ^a   Wang, Yuanyuan ^a   Zhang, Jialing ^a   Yu, Zhi Xiang ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

Cycloaddition; Density functional calculations; Fused ring systems; Homogeneous catalysis; Rhodium

Indexed keywords

CYCLOOCTENONES; DENSITY-FUNCTIONAL CALCULATIONS; FUSED-RING SYSTEM; HOMOGENEOUS CATALYSIS; ONE-POT SYNTHESIS; RING SYSTEMS; TWO-COMPONENT;

CATALYSIS; ENERGY ABSORPTION; REACTION KINETICS; RHODIUM COMPOUNDS;

RHODIUM;

EID: 77954344644     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000053     Document Type: Article

References (86)

1. a) P. A. Wender, B. L. Miller, Organic Synthesis: Theory and Applications, Vol. 2, (Ed: T. Hudlicky), JAI, Greenwich, 1993, pp. 27-66;
2. M. Malacria, Chem. Rev. 1996, 96, 289;
3. P. Kündig, Science 2006, 314, 430.
4. a) B. M. Trost, Angew. Chem. 1995, 107, 285;
5. Angew. Chem. Int. Ed. Engl. 1995, 34, 259;
6. P. A. Wender, S. T. Handy, D. L. Wright, Chem. Ind. 1997, 765;
7. P. A. Wender, F. C. Bi, G. G. Gamber, F. Gosselin, R. D. Hubbard, M. J. C. Scanio, R. Sun, T. J. Williams, L. Zhang, Pure Appl. Chem. 2002, 74, 25.
8. For recent reviews on transition-metal-catalyzed cycloadditions, see:a) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49;
9. H.-W. Frühauf, Chem. Rev. 1997, 97, 523;
10. M. A. J. Duncton, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1999, 1235;
11. L. Yet, Chem. Rev. 2000, 100, 2963;
12. S. Saito, Y. Yamamoto, Chem. Rev. 2000, 100, 2901;
13. C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813;
14. M. Murakami, Angew. Chem. 2003, 115, 742;
15. Angew. Chem. Int. Ed. 2003, 42, 718;
16. S. E. Gibson, N. Mainolfi, Angew. Chem. 2005, 117, 3082;
17. Angew. Chem. Int. Ed. 2005, 44, 3022.
18. a) N. A. Petasis, M. A. Patane, Tetrahedron 1992, 48, 5757;
19. S. M. Sieburth, N. T. Cunard, Tetrahedron 1996, 52, 6251;
20. G. Mehta, V. Singh, Chem. Rev. 1999, 99, 881;
21. A. Michaut, J. Rodriguez, Angew. Chem. 2006, 118, 5870;
22. Angew. Chem. Int. Ed. 2006, 45, 5740.
23. a) P. A. Wender, N. C. Ihle, J. Am. Chem. Soc. 1986, 108, 4678;
24. P. A. Wender, A. G. Correa, Y. Sato, R. Sun, J. Am. Chem. Soc. 2000, 122, 7815;
25. Y. Chen, R. Kiattansakul, B. Ma, J. K. Snyder, J. Org. Chem. 2001, 66, 6932;
26. B. Ma, J. K. Snyder, Organometallics 2002, 21, 4688;
27. P. A. Evans, J. E. Robinson, E. W. Baum, A. N. Fazal, J. Am. Chem. Soc. 2002, 124, 8782;
28. P. A. Wender, G. G. Gamber, R. D. Hubbard, L. Zhang, J. Am. Chem. Soc. 2002, 124, 2876;
29. S. R. Gilbertson, B. De Boef, J. Am. Chem. Soc. 2002, 124, 8784;
30. J. A. Varela, J. A. L. Castedo, C. Saa, Org. Lett. 2003, 5, 2841;
31. P. A. Evans, E. W. Baum, A. N. Fazal, M. Pink, Chem. Commun. 2005, 63;
32. H. A. Wegner, A. de Meijere, P. A. Wender, J. Am. Chem. Soc. 2005, 127, 6530;
33. P. A. Wender, J. P. Christy, J. Am. Chem. Soc. 2006, 128, 5354;
34. M. Murakami, S. Ashida, T. Matsuda, J. Am. Chem. Soc. 2006, 128, 2166;
35. Z. Chai, H. Wang, G. Zhao, Synlett 2009, 11, 1785;
36. P. A. Wender, J. P. Christy, A. B. Lesser, M. T. Gieseler, Angew. Chem. 2009, 121, 7823;
37. Angew. Chem. Int. Ed. 2009, 48, 7687;
38. Y. Kuninobu, A. Kawata, M. Nishi, S. S. Yudha, J. Chen, K. Takai, Chem. Asian J. 2009, 4, 1424.
39. For a recent review, see: p) Z.-X. Yu, Y. Wang, Y. Wang, Chem. Asian J. 2010, DOI:10.1002/asia.200900712.
40. a) Y. Wang, J. Wang, J. C. Su, F. Huang, L. Jiao, Y. Liang, D. Z. Yang, S. W. Zhang, P. A. Wender, Z.-X. Yu, J. Am. Chem. Soc. 2007, 129, 10060.
41. For application of the [(5+2) +1] cycloaddition in total synthesis, see: b) L. Jiao, C. Yuan, Z.-X. Yu, J. Am. Chem. Soc. 2008, 130, 4421;
42. X. Fan, M.-X. Tang, L.-G. Zhuo, Y. Q. Tu, Z.-X. Yu, Tetrahedron Lett. 2009, 50, 155;
43. X. Fan, L.-G. Zhuo, Y. Q. Tu, Z.-X. Yu, Tetrahedron 2009, 65, 4709.
44. We suggest here a new nomenclature system for transition-catalyzed cycloaddition reactions. For three-component cycloaddition of vinylcyclopropanes, alkynes, and CO, this is named as a [5+2+1] cycloaddition. [5b] For the two-component cycloaddition of ene-VCPs and CO, 6 this is named as a [(5+2) +1] cycloaddition, where the (5+2) part comes from one molecule, ene-VCP.
45. M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325.
46. a) S. Huneck, G. Baxter, A. F. Cameron, J. D. Connelly, D. S. Rycroft, Tetrahedron Lett. 1983, 24, 3787;
47. J. Zapp, G. Burkhardt, H. Becker, Phytochemistry 1994, 37, 787;
48. H.-J. Liu, C.-L. Wu, H. Becker, J. Zapp, Phytochemistry 2000, 53, 845.
49. a) S. Nozoe, M. Morisaki, K. Tsuda, Y. Iitaka, N. Takahashi, S. Tamura, K. Ishibashi, M. Shirasaka, J. Am. Chem. Soc. 1965, 87, 4968;
50. L. Erguang, A. M. Clark, D. P. Rotella, C. D. Hufford, J. Nat. Prod. 1995, 58, 74.
51. a) L. A. Paquette, J. Am. Chem. Soc. 1993, 115, 1676;
52. L. A. Paquette, L.-Q. Sun, D. Freidrich, P. B. Savage, Tetrahedron Lett. 1997, 38, 195;
53. B. Salem, J. Suffert, Angew. Chem. 2004, 116, 2886;
54. Angew. Chem. Int. Ed. 2004, 43, 2826;
55. S. J. Bader, M. L. Snapper, J. Am. Chem. Soc. 2005, 127, 1201;
56. Y.-D. Zhang, W.-W. Ren, Y. Lan, Q. Xiao, K. Wang, J. Xu, J.-H. Chen, Z. Yang, Org. Lett. 2008, 10, 665;
57. For a diradical approach to construct a taxol skeleton in one operation, see: f) P. J. Mikesell, R. D. Little, Tetrahedron Lett. 2001, 42, 4095.
58. For selected total synthesis of natural products with [5-8-5] ring systems, see:a) N. Kato, H. Takeshita, H. Kataoka, S. Ohbuchi, S. J. Tanaka, J. Chem. Soc. Perkin Trans. 1 1989, 165 and references therein;
59. M. Rowley, M. Tsukamoto, Y. Kishi, J. Am. Chem. Soc. 1989, 111, 2735;
60. R. K. Boeckman, Jr., A. Arvanitis, M. E. Voss, J. Am. Chem. Soc. 1989, 111, 2737;
61. T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505;
62. H. Okamoto, H. Arita, N. Kato, H. Takeshita, Chem. Lett. 1994, 2335;
63. P. A. Wender, M. J. Nuss, D. B. Smith, A. Suarez-Sobrino, J. Vagberg, D. Decosta, J. Bordner, J. Org. Chem. 1997, 62, 4908;
64. L. A. Paquette, L. Q. Sun, D. Friedrich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438;
65. D. R. Williams, L. A. Robinson, C. R. Nevill, J. P. Reddy, Angew. Chem. 2007, 119, 933;
66. Angew. Chem. Int. Ed. 2007, 46, 915.
67. For selected total synthesis of taxol:a) R. A. Holton, C. Somoza, H. B. Kim, F. Liang, R. J. Beidiger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, J. Am. Chem. Soc. 1994, 116, 1597;
68. R. A. Holton, C. Somoza, H. B. Kim, F. Liang, R. J. Beidiger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, J. Am. Chem. Soc. 1994, 116, 1599;
69. K. C. Nicolaou, Z. Yang, J. J. Liu, H. Ueno, P. G. Nantermet, R. K. Guy, C. F. Claiborne, J. Renaud, E. A. Couladouros, K. Paulvannan, E. J. Sorensen, Nature 1994, 367, 630;
70. S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A Coburn, M J. D. Grandi, J. Am. Chem. Soc. 1996, 118, 2843;
71. P. A. Wender, N. F. Badham, S. P. Conway, P. E. Floreancig, T. E. Glass, C. Gränicher, J. B. Houze, J. Jänichen, D. Lee, D. G. Marquess, P. L. McGrane, W. Meng, T. P. Mucciaro, M. Mühlebach, M. G. Natchus, H. Paulsen, D. B. Rawlins, J. Satkofsky, A. J. Shuker, J. C. Sutton, R. E. Taylor, K. Tomooka, J. Am. Chem. Soc. 1997, 119, 2755;
72. K. Morihira, R. Hara, S. Kawahara, T. Nishimori, N. Nakamura, H. Kusama, I. Kuwajima, J. Am. Chem. Soc. 1998, 120, 12980;
73. H. Kusama, R. Hara, S. Kawahara, T. Nishimori, H. Kashima, N. Nakamura, K. Morihira, I. Kuwajima, J. Am. Chem. Soc. 2000, 122, 3811.
74. For one-pot synthesis of [5-7-5] and [5-7-6] ring systems, see:a) B. M. Trost, F. D. Toste, H. Shen, J. Am. Chem. Soc. 2000, 122, 2379;
75. B. M. Trost, H. Shen, Angew. Chem. 2001, 113, 2375;
76. Angew. Chem. Int. Ed. 2001, 40, 2313;
77. B. M. Trost, H. Shen, D. B. Horne, F. D. Toste, B. G. Steinmetz, C. Koradin, Chem. Eur. J. 2005, 11, 2577.
78. 298K) at 298 K in the gas phase.
79. 2-catalyzed [5+2] and [(5+2) +1] cycloadditions with catalytic species of [Rh (CO) Cl] occurs through cyclopropane cleavage, alkene insertion, CO coordination, alkyl migration, and reductive elimination; see:a) Z.-X. Yu, P. A. Wender, K. N. Houk, J. Am. Chem. Soc. 2004, 126, 9154;
80. ref. 6;
81. 2Cl], depending on the reaction conditions; see: H. Wang, J. R. Sawyer, P. A. Evans, M.-H. Baik, Angew. Chem. 2008, 120, 348;
82. Angew. Chem. Int. Ed. 2008, 47, 342.
83. For a recent review of computational prediction of new catalysts and reactions, see: K. N. Houk, P. H.-Y. Cheong, Nature 2008, 455, 309.
84. For recent reviews on asymmetric cyclopropanation, see:a) A. H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341;
85. A. Pfaltz in Comprehensive Asymmetric Catalysis II (Eds.: E. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 513-538;
86. For a recent example of enantiomerically enriched VCP participating in a reaction, see: L. Jiao, S. Ye, Z.-X. Yu, J. Am. Chem. Soc. 2008, 130, 7178.