An efficient route to benzene and phenol derivatives via ring-closing olefin metathesis

Synlett

Volumn , Issue 10, 2007, Pages 1561-1564

  Yoshida, Kazuhiro ^a   Horiuchi, Shingo ^a   Iwadate, Noriyuki ^a   Kawagoe, Fumihiro ^a   Imamoto, Tsuneo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Annulations; Metathesis; Ring closure; Ruthenium; Tautomerism

Indexed keywords

ALKENE DERIVATIVE; BENZENE DERIVATIVE; PHENOL DERIVATIVE;

ANNULATION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; RING CLOSING METATHESIS;

EID: 34347353329     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-982548     Document Type: Article

References (29)

1. For a review, see: Donohoe, T. J.; Orr, A. J.; Bingham, M. Angew. Chem. Int. Ed. 2006, 45, 2664.
2. For reports on the direct synthesis of carbocyclic aromatic compounds using RCM, see: (a) Iuliano, A.; Piccioli, P.; Fabbri, D. Org. Lett. 2004, 6, 3711.
3. (b) Walker, E. R.; Leung, S. Y.; Barrett, A. G. M. Tetrahedron Lett. 2005, 46, 6537.
4. (c) Pelly, S. C.; Parkinson, C. J.; Van Otterlo, W. A. L.; De Koning, C. B. J. Org. Chem. 2005, 70, 10474.
5. For reports on the RCM-elimination protocol, see: (d) Evans, P.; Grigg, R.; Ramzan, M. I.; Sridharan, V.; York, M. Tetrahedron Lett. 1999, 40, 3021.
6. (e) Huang, K. S.; Wang, E. C. Tetrahedron Lett. 2001, 42, 6155.
7. (f) Chen, Y.; Dias, H. V. R.; Lovely, C. J. Tetrahedron Lett. 2003, 44, 1379.
8. (g) Yoshida, K.; Kawagoe, F.; Iwadate, N.; Takahashi, H.; Imamoto, T. Chem. Asian J. 2006, 1, 611.
9. For a report on the RCM-oxidation protocol, see: (h) Kotha, S.; Mandal, K. Tetrahedron Lett. 2004, 45, 2585.
10. For reports on the RCM-tautomerization protocol, see: (i) van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311.
11. (j) Yoshida, K.; Imamoto, T. J. Am. Chem. Soc. 2005, 127, 10470.
12. (a) Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55.
13. (b) Llebaria, A.; Camps, F.; Moreto, J. M. Tetrahedron 1993, 49, 1283.
14. (c) Bäckvall, J.-E.; Nilsson, Y. I. M.; Gatti, R. G. P. Organometallics 1995, 14, 4242.
15. (d) Thadani, A. N.; Rawal, V. H. Org. Lett. 2002, 4, 4317.
16. Tessier, P. E.; Penwell, A. J.; Souza, F. E. S.; Fallis, A. G. Org. Lett. 2003, 5, 2989.
17. Taylor, R. E.; Ciavarri, J. P. Org. Lett. 1999, 1, 467.
18. 3 was performed.
19. The stereoselective hydroalumination of propargyl alcohol followed by allylation developed by Langille and Jamison was employed only for the synthesis of 8b and 8g, see: Langille, N. F.; Jamison, T. F. Org. Lett. 2006, 8, 3761.
20. +]: 240.1150; found: 240.1152.
21. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
22. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
23. (c) Belderrain, T. R.; Grubbs, R. H. Organometallics 1997, 16, 4001.
24. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
25. (b) Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T.-L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 2546.
26. +]: 256.1099; found: 256.1095.
27. (a) Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem. Int. Ed. 2002, 41, 4035.
28. (b) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
29. (c) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8.