Rhodium-catalyzed carbonylative [3+3+1] cycloaddition of biscyclopropanes with a vinyl substituent to form seven-membered rings

Angewandte Chemie - International Edition

Volumn 47, Issue 26, 2008, Pages 4914-4917

  Kim, Sun Young ^a   Lee, Sang Ick ^a   Choi, Soo Young ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

Carbonylation; Cycloaddition; Cyclopropanes; Rhodium; Seven membered rings

Indexed keywords

CHEMICAL REACTIONS; DIFFERENCE EQUATIONS; DIFFERENTIATION (CALCULUS); RHODIUM;

CARBONYLATION; CYCLOADDITION; CYCLOPROPANES; SEVEN-MEMBERED RINGS;

RHODIUM COMPOUNDS;

CYCLOPROPANE DERIVATIVE; RHODIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION;

CATALYSIS; CYCLIZATION; CYCLOPROPANES; MOLECULAR STRUCTURE; RHODIUM; VINYL COMPOUNDS;

EID: 48849086704     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800432     Document Type: Article

References (48)

1. a) M. A. Battiste, P. M. Pelphrey, D. L. Wright, Chem. Eur. J. 2006, 12, 3438-3447;
2. b) G. Rousseau, F. Homsi, Chem. Soc. Rev. 1997, 26, 453-461.
3. a) Y. R. Lee, J. C. Hwang, Eur. J. Org. Chem. 2005, 1568-1577;
4. b) G. Prié, N. Prevost, H. Twin, S. A. Fernandes, J. F. Hayes, M. Shipman, Angew. Chem. 2004, 116, 6679-6681;
5. Angew. Chem. Int. Ed. 2004, 43, 6517-6519;
6. c) J. A. Saez, M. Arno, L. R. Domingo, Org. Lett. 2003, 5, 4117-4120;
7. d) M. Harmata, U. Sharma, Org. Lett. 2000, 2, 2703-2705;
8. e) B. M. Trost, S. Yamazaki, Chem. Lett. 1994, 2245-2248.
9. a) P. A. Wender, L. O. Haustedt, J. Lim, J. A. Love, T. J. Williams, J.-Y. Yoon, J. Am. Chem. Soc. 2006, 128, 6302-6303;
10. b) P. A. Wender, G. G. Gamber, T. J. Williams in Modern Rhodium-Catalyzed Organic Reactions (Ed.: P. A. Evans), Wiley-VCH, Weinheim, 2005, chap. 13, pp. 263-299;
11. c) H. A. Wegner, A. de Meijere, P. A. Wender, J. Am. Chem. Soc. 2005, 127, 6530-6531;
12. d) B. M. Trost, H. C. Shen, D. B. Horne, F. D. Toste, B. G. Steinmetz, C. Koradin, Chem. Eur. J. 2005, 11, 2577-2590;
13. e) P. A. Wender, T. M. Pedersen, M. J. C. Scanio, J. Am. Chem. Soc. 2002, 124, 15154-15155;
14. f) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349;
15. g) P. A. Wender, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1998, 120, 1940-1941;
16. h) P. A. Wender, H. Takahashi, B. Witulski, J. Am. Chem. Soc. 1995, 117, 4720-4721.
17. P. A. Wender, N. M. Deschamps, R. Sun, Angew. Chem. 2006, 118, 4061-4064;
18. Angew. Chem. Int. Ed. 2006, 45, 3957-3960.
19. Y. Ni, J. Montgomery, J. Am. Chem. Soc. 2004, 126, 11162-11163.
20. a) S. Saito, S. Komagawa, I. Azumaya, M. Masuda, J. Org. Chem. 2007, 72, 9114-9120;
21. b) S. Komagawa, S. Saito, Angew. Chem. 2006, 118, 2506-2509;
22. Angew. Chem. Int. Ed. 2006, 45, 2446-2449;
23. c) S. Saito, M. Matsuda, S. Komagawa, J. Am. Chem. Soc. 2004, 126, 10540-10541;
24. d) P. Binger, A. Brinkmann, P. Wedemann, Chem. Ber. 1983, 116, 2920-2930;
25. e) P. Binger, U. Schuchardt, Chem. Ber. 1980, 113, 1063-1071;
26. f) P. Binger, A. Brinkmann, J. McMeeking, Justus Liebigs Ann. Chem. 1977, 1065-1079.
27. B. Bennacer, M. Fujiwara, S.-Y. Lee, I. Ojima, J. Am. Chem. Soc. 2005, 127, 17756-17767.
28. a) C. Bruneau, Angew. Chem. 2005, 117, 2380-2386;
29. Angew. Chem. Int. Ed. 2005, 44, 2328-2334;
30. b) C. Nieto-Oberhuber, S. López, E. Jimnez-Núñez, A. M. Echavarren, Chem. Eur. J. 2006, 12, 5916-5923;
31. c) C. Nieto-Oberhuber, S. López, M. P. Muñoz, E. Jimnez-Núñez, E. Buñuel, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1694-1702.
32. a) A. de Meijere, S. I. Kozhushkov, H. Schill, Chem. Rev. 2006, 106, 4926-4996;
33. b) A. Brandi, A. Goti, Chem. Rev. 1998, 98, 589-635.
34. a) X. Huang, Y. Yang, Org. Lett. 2007, 9, 1667-1670;
35. b) B. Trillo, M. Gulias, F. Lopez, L. Castedo, J. L. Mascarenas, Adv. Synth. Catal. 2006, 348, 2381-2384;
36. c) A. I. Siriwardana, M. Kamada, I. Nakamura, Y. Yamamoto, J. Org. Chem. 2005, 70, 5932-5937;
37. d) H. Liu, C. A. Shook, J. A. Jamison, M. Thiruvazhi, T. Cohen, J. Am. Chem. Soc. 1998, 120, 605-606;
38. e) S. Sarel, Acc. Chem. Res. 1978, 11, 204-211.
39. P. A. Wender, C. M. Barzilay, A. J. Dyckman, J. Am. Chem. Soc. 2001, 123, 179-180.
40. a) C. Nieto-Oberhuber, M. P. Muñoz, S. López, E. Jiménez-Núñez, C. Nevado, E. Herrero-Gómez, M. Raducan, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1677-1693;
41. b) S. I. Lee, S. M. Kim, M. R. Choi, S. Y. Kim, Y. K. Chung, W.-S. Han, S. W. Kang, J. Org. Chem. 2006, 71, 9366-9372;
42. c) C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
43. Angew. Chem. Int. Ed. 2004, 43, 2402-2406;
44. d) A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2001, 123, 11863-11869;
45. e) M. Mendez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520;
46. f) A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785-6786.
47. The synthetic procedures and spectroscopic data of new compounds are summarized in the Supporting Information. CCDC 655707 (1E) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data_request/cif.
48. R. G. Salomon, M. F. Salomon, J. L. C. Kachinski, J. Am. Chem. Soc. 1977, 99, 1043-1054.