Tetrahydrothiophene-catalyzed synthesis of benzo[n.1.0] bicycloalkanes

Journal of Organic Chemistry

Volumn 72, Issue 4, 2007, Pages 1335-1340

  Ye, Long Wu ^a   Sun, Xiu Li ^a   Li, Chuan Ying ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; REACTION KINETICS; STEREOCHEMISTRY; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

BENZOBICYCLIC COMPOUNDS; CYCLOPROPANATION; STEREOSELECTIVITY; TETRAHYDROTHIOPHENE;

PARAFFINS;

BICYCLO COMPOUND; CYCLOALKANE DERIVATIVE; TETRAHYDROTHIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOPROPANATION; ORGANIC CHEMISTRY; STEREOCHEMISTRY;

EID: 33847002748     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062209m     Document Type: Article

References (51)

1. (a) Srikrishna, A.; Anebouselvy, K. J. Org. Chem. 2001, 66, 7102.
2. (b) Guella, G.; Skropeta, D.; Breuils, S.; Mancini, I.; Pietra, F. Tetrahedron Lett. 2001, 42, 723.
3. (c) Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745.
4. (d) Lee, E.; Shin, I. J.; Kim, T. S. J. Am. Chem. Soc. 1990, 112, 260.
5. (a) Anquetin, G.; Rouquayrol, M.; Mahmoudi, N.; Santillana-Hayat, M.; Gozalbes, R.; Greiner, J.; Farhati, K.; Derouin, F.; Guedj, R.; Vierling, P. Bioorg. Med. Chem. Lett. 2004, 14, 2773.
6. (b) Lee, W.; Miller, M. J. J. Org. Chem. 2004, 69, 4516.
7. (c) Wang, T.-Z.; Pinard, E.; Paquette, L. A. J. Am. Chem. Soc. 1996, 118, 1309.
8. (a) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
9. (b) Sarpong, R.; Su, J. T.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 13624.
10. (c) Braña, M. F.; Guisado, C.; Alguacil, L. F.; Garrido, E.; Pérez-García, C.; Ruiz-Gayo, M. Bioorg. Med. Chem. Lett. 2002, 12, 3561.
11. (d) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
12. (e) Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941.
13. (a) Miura, T.; Sasaki, T.; Harumashi, T.; Murakami, M. J. Am. Chem. Soc. 2006, 128, 2516.
14. (b) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriěs, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
15. (c) Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858.
16. (d) Porta, E. L.; Piarulli, U.; Cardullo, F.; Paio, A.; Provera, S.; Seneci, P.; Gennari, C. Tetrahedron Lett. 2002, 43, 761.
17. (e) Yang, D.; Gao, Q.; Lee, C.-S.; Cheung, K.-K. Org. Lett. 2002, 4, 3271.
18. (a) Honma, M.; Sawada, T.; Fujisawa, Y.; Utsugi, M.; Watanabe, H.; Umino, A.; Matsumura, T.; Hagihara, T.; Takano, M.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 2860.
19. (b) Tokunoh, R.; Tomiyama, H.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 2449.
20. (c) Mass, G. Chem. Soc. Rev. 2004, 3, 183.
21. (a) Clive, D. L. J.; Daigneault, S. J. Org. Chem. 1991, 56, 3801.
22. (b) Clive, D. L. J.; Daigneault, S. J. Chem. Soc., Chem. Commun. 1989, 332.
23. (c) Payne, G. B. J. Org. Chem. 1967, 32, 3351.
24. (a) Johansson, C. C. C.; Bremeyer, N.; Ley, S. V.; Owen, D. R.; Smith, S. C.; Gaunt, M. J. Angew. Chem., Int. Ed. 2006, 45, 6024.
25. (b) Bremeyer, N.; Smith, S. C.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 2681.
26. For ylide cyclopropanation, please see: (a) Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X. J. Am. Chem. Soc. 2006, 128, 9730.
27. (b) Zheng, J.-C.; Liao, W.-W.; Tang, Y.; Sun, X.-L.; Dai, L.-X. J. Am. Chem. Soc: 2005, 127, 12222.
28. (c) Jiang, H.; Deng, X.-M.; Sun, X.-L.; Tang, Y.; Dai, L.-X. J. Org. Chem. 2005, 70, 10202.
29. (d) Liao, W.-W.; Li, K.; Tang, Y. J. Am. Chem. Soc. 2003, 125, 13030.
30. (e) Ye, S.; Huang, Z.-Z.; Xia, C.-A.; Tang, Y.; Dai, L.-X. J. Am. Chem. Soc. 2002, 124, 2432.
31. For ylide aziridination and epoxidation, see: (f) Zheng, J.-C.; Liao, W.-W.; Sun, X.-X.; Sun, X.-L.; Tang, Y.; Dai, L.-X.; Deng, J. G. Org. Lett. 2005, 7, 5789.
32. (g) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516.
33. (h) Li, K.; Deng, X.-M.; Tang, Y. Chem. Commun. 2003, 2074.
34. Ye, L.-W.; Sun, X.-L.; Zhu, C.-Y.; Tang, Y. Org. Lett. 2006, 8, 3853.
35. For reviews on ylide cyclopropanation, please see: (a) Ye, S.; Tang, Y.; Sun, X.-L. Synlett 2005, 2720.
36. (b) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
37. (c) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
38. (d) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
39. For recent examples, see: (e) Aggarwal, V. K.; Grange, E. Chem. Eur. J. 2006, 12, 568.
40. (f) Kunz, R. K.; Macmillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
41. (g) Huang, K.; Huang, Z.-Z. Synlett 2005, 1621.
42. (h) Mikołajczyk, M.; Midura, W. H.; Michedkina, E.; Filipczak, A. D.; Wieczorek, M. W. Helv. Chim. Acta 2005, 88, 1769.
43. Tamura, Y.; Taniguchi, H.; Miyamoto, T.; Tsunekawa, M.; Ikeda, M. J. Org. Chem. 1974, 39, 3518.
44. Huang, Y.-Z.; Tang, Y.; Zhou, Z.-L.; Xia, W.; Shi, L.-P. J. Chem. Soc., Perkin Trans. 1 1994, 7, 893.
45. (a) Aurrecoechea, J. M.; López, B.; Fernandez, A.; Arrieta, A.; Cossío, F. P. J. Org. Chem. 1997, 62, 1125.
46. (b) Mori, K.; Tanaka, T. I.; Honda, H.; Yamamoto, I. Tetrahedron 1983, 39, 2303.
47. (a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
48. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
49. 3 for a few minutes and, thus, the pure desired products could be obtained easily. (Chemical Equation Presented).
50. Cordi, A. A.; Berque-Bestel, I.; Persigand, T.; Lacoste, J. M.; Newman-Tancredi, A.; Audinot, V.; Millan, M. J. J. Med. Chem. 2001, 44, 787.
51. Löffler, F.; Hagen, M.; Lüning, U. Synlett 1999, 1826.