Stereoselective generation of Cis or trans olefins from the RuCl2(PPh3)3-catalyzed diazo coupling of thyldiazoacetate

Organometallics

Volumn 21, Issue 18, 2002, Pages 3823-3826

  Graban, Eric ^a   Lemke, Frederick R ^a  

^a OHIO UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZO COUPLING;

CATALYSIS; COMPLEXATION; OLEFINS; RUTHENIUM;

STEREOCHEMISTRY;

EID: 0037820394     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020271d     Document Type: Article

References (43)

1. Pellicciari, R.; Natalini, B.; Marinozzi, M.; Monahan, J. B.; Snyder, J. P. Tetrahedron Lett. 1990, 31, 139-142.
2. Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247-1262.
3. Anciaux, A. J.; Hubert, A, J.; Noels, A. P.; Petiniot, N.; Teysaié, P. J. Org. Chem. 1980, 45, 695-702.
4. Zhou, S.-M.; Deng, M.-Z.; Xia, L.-J.; Tang, M.-H. Angew. Chem., Int. Ed. 1998, 37, 2845-2847.
5. Smith, D. A.; Reynolds, D. N.; Woo, L. K. J. Am. Chem. Soc. 1998, 115, 2511-2513.
6. Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 776, 2223-2224.
7. Singh, V. K.; DattaGupta, A.; Sekar, G, Synthesis 1997, 137-149.
8. Lo, W.-C.; Che, C.-M.; Cheng, K.-F.; Mak, T. C. W. Chem. Commun. 1997, 1205-1206.
9. Galardon, E.; Le Maux, P.; Simonneaux, G. Chem. Commun. 1997, 927-928.
10. Wright, M. E.; Svejda, S. A.; Jin, M.-J.; Peterson, M. A. Organometallics 1990, 9, 136-146.
11. Collman, J. P.; Brothers, P. J.; McElwee-White, L.; Rose, E. J. Am. Chem. Soc. 1985, 707, 6110-6111.
12. Rasmussen, K. G.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans, 1 1997, 1287-1291.
13. Hansen, S. M.; Wolland, A. O.; Rominger, F.; Eisentrager, F.; Hofman, P. Angew. Chem., Int. Ed. 1999, 38, 1273-1276.
14. Wolf, J.; Stüer, W.; Grünwald, C.; Werner, H.; Schwab, P.; Schulz, M. Angew. Chem., Int. Ed. 1998, 37, 1124-1126.
15. Collman, J. P.; Brothers, P. J.; McElwee-White, L.; Rose, E.; Wright, L. J. J. Am. Chem. Soc. 1985, 707, 4570-4571.
16. Nishiyama, H.; Park, S.-B.; Haga, M.-A.; Aoki, K.; Itoh, K. Chem. Lett. 1994, 1111-1114.
17. Vallgårda, J.; Appelberg, U.; Csöregh, L; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1994, 461-470.
18. Djukic, J.-P.; Smith, D. A.; Young, J.; Victor, G.; Woo, L. K. Organometallics 1994, 13, 3020-3026.
19. Masters, C.; van der Woude, C.; van Doorn, J. A. J. Am. Chem. Soc. 1979, 707, 1633-1634.
20. Baratta, W.; Del Zotto, A.; Rigo, P. Chem. Commun. 1997, 2163-2164.
21. Baratta, W.; Del Zotto, A.; Rigo, P. Organometallics 1999, 18, 5091-5096.
22. Simunic, J. L.; Pinhas, A. R. Inorg. Chem. 1989, 28, 2400-2406.
23. Díaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Prieto, F.; Pérez, P. J. Organometallics 1999, 18, 2601-2609.
24. Kubo, J.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 625-626.
25. Woo, L. K.; Smith, D. A. Organometallics 1992, 11, 2344-2346.
26. Berry, D. H.; Koloski, T. S.; Carroll, P. J. Organometallics 1990, 9, 2952-2962.
27. Schrook, R. R.; Sharp, P. R. J. Am. Chem. Soc. 1978, 100, 2389-2399.
28. Merrifield, J. H.; Lin, G.-Y.; Kiel, W. A.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 5811-5819.
29. Roger, C.; Bodner, G. S.; Hatten, W. G,; Gladysz, J. A. Organometallica 1991, 10, 3266-3274.
30. Casey, C. P.; Anderson, R. L. J. Chem. Soc., Chem. Commun. 1975, 895-896.
31. Baratta, W.; Herrmann, W. A.; Kratzer, R. M.; Rigo, P. Organometallics 2000, 19, 3664-3669.
32. Bianchini, C.; Lee, H. M. Organometallics 2000, 19, 1833-1840.
33. Lee, H. M.; Bianchini, C.; Jia, G.; Barbaro, P. Organometallics 1999, 18, 1961-1966.
34. Collman, J. P.; Rose, E.; Venburg, G. D. J. Chem. Soc., Chem. Commun. 1998, 934-935.
35. Park, S.-B.; Nishiyama, H.; Itoh, Y.; Itoh, K. J. Chem. Soc., Chem. Commun. 1994, 1315-1316.
36. Galardon, E.; Le Maux, P.; Toupet, L.; Simonneaux, G. Organometallica 1998, 17, 565-569.
37. Le Paih, J.; Derien, S.; Ozdemir, I.; Dixneuf, P. H. J. Am. Chem. Soc. 2000, 122, 7400-7401.
38. Demonceau, A.; Lemoine, C. A.; Noels, A, F.; Chizhevsky, I. T.; Sorokin, P. V. Tetrahedron Lett. 1998, 36, 8419- 8422.
39. Yardy, N. M.; Lemke, F. R. Main Group Chem. 2000, 3, 143-147.
40. Yardy, N. M. Dichlorotris(triphenylphosphine)ruthenium(II): Reactions with Tertiary-Hydrosilanes and the Catalytic Hydrosilylation of Phenylacetylene. Ph.D. Dissertation, Ohio University, Athens, OH, 2001.
41. James, B. R.; Markham, L. D. Inorg. Chem. 1974, 73, 97-100.
42. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc 1993, 115, 9856-9857.
43. Trnka, T. M.; Grubbs, R. H. Ace. Chem. Res. 2001, 34, 18-29.