Highly selective intra- and intermolecular coupling reactions of diazo compounds to form cis-alkenes using a ruthenium porphyrin catalyst

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1621-1623

  Li, Gong Yong ^a   Che, Chi Ming ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AZO COMPOUND; PATULOLIDE B; RUTHENIUM DERIVATIVE; RUTHENIUM PORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ISOMER; SYNTHESIS;

EID: 2542569635     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049626a     Document Type: Article

References (33)

1. (a) Grundman, C. J. Liebigs Ann. Chem. 1938, 536, 2936.
2. (b) Ernest, I.; Stanek, J. Collect. Czech. Chem. Commun. 1959, 24, 530.
3. (c) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R. J. Org. Chem. 1985, 50, 3322.
4. (d) Oshima, T.; Nagar, T. Tetrahedron Lett. 1980, 21, 1251.
5. (e) Shankar, B. K. R.; Shechter, H. Tetrahedron Lett. 1982, 23, 2277.
6. (f) Font, J.; Serratosa, F.; Valls, J. J. Chem. Soc., Chem. Commun. 1970, 721.
7. (g) Kulkowit, S.; McKervey, M. A. J. Chem. Soc., Chem. Commun. 1978, 1069.
8. (h) Woo, L. K.; Smith, D. A. Organometallics 1992, 11, 2344.
9. (i) Collman, J. P.; Rose, E.; Venburg, G. D. J. Chem. Soc., Chem. Commun. 1993, 934.
10. (j) Park, S.-B.; Nishiyama, H.; Itoh, Y.; Ito, K. J. Chem. Soc., Chem. Commun. 1994, 1315.
11. (k) Baratta, W.; Del Zotto, A.; Rigo, P. Chem. Commun. 1997, 2163.
12. (l) Galardon, E.; Le Maux, P.; Toupet, L.; Simonneaux, G. Organometallics 1998, 17, 565.
13. (m) Lee, H. M.; Bianchini, C.; Jia, G.; Barbaro, P. Organometallics 1999, 18, 1961.
14. (n) Diaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Prieto, F.; Pérez, P. J. Organometallics 1999, 18, 2601.
15. (o) Baratta, W.; Del Zotto, A.; Rigo P. Organometallics 1999, 18, 5091.
16. (p) Del Zotto, A.; Baratta, W.; Verardo, G.; Rigo, P. Eur. J. Org. Chem. 2000, 2795.
17. (q) Doyle, M. P.; Hu, W.; Phillips, L. M. Org. Lett. 2000, 2, 1777.
18. (r) Davis, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063.
19. (s) Graban, E.; Lemke, F. R. Organometallics 2002, 21, 3823.
20. (a) Lo, W.-C.; Che, C.-M.; Cheng, K.-F.; Mak, T. C. W. Chem. Commun. 1997, 1206.
21. (b) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-R; Lee, W.-S.; Lo, W.-C.; Peng, S.-M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119.
22. Li, G.-Y.; Chen, J.; Yu, W.-Y.; Hong, W.; Che, C.-M. Org. Lett. 2003, 5, 2153.
23. Zhou, C.-Y.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2002, 4, 3235.
24. For preparation of 1, see: Leung, W.-H.; Che, C.-M.; Yeung, C.-H.; Poon, C.-K. Polyhedron 1993, 12, 2331.
25. (a) Sekiguchi, J.; Kuruda, H.; Yamada, Y.; Okada, H. Tetrahedron Lett. 1985, 26, 2341.
26. (b) Rodphya, D.; Sekiguchi, J.; Yamada, Y. J. Antibiot. 1986, 39, 629.
27. Makita, A.; Yamada, Y.; Okada, H. J. Antibiot. 1986, 39, 1259.
28. (a) Kalita, D.; Khan, A. T.; Barua, N. C.; Bez, G. Tetrahedron 1999, 55, 5177.
29. (b) Bestmann, H. J.; Kellermann, W.; Pecher, B. Synthesis 1993, 149.
30. (c) Solladié, G.; Gerber, C. Synlett 1992, 449.
31. (d) Mori, K.; Sakai, T. Liebigs Ann. Chem. 1988, 13.
32. (e) Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem. 1998, 63, 7505.
33. Ronsheim, M. D.; Zercher, C. K. J. Org. Chem. 2003, 68, 1878.