Homologation of monoterpenoids into new sesquiterpenoids via tandem isomerisation/claisen rearrangement reactions with three-component ruthenium catalysts, and Ru(methallyl)2 (COD) revealed by high throughput screening techniques

Advanced Synthesis and Catalysis

Volumn 347, Issue 6, 2005, Pages 783-791

  Le Nôtre, Jérôme ^a   Touzani, Rachid ^a,b   Lavastre, Olivier ^a,b   Bruneau, Christian ^a   Dixneuf, Pierre H ^a  

^a UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

^b Institut de Chimie de Rennes   (France)

Author keywords

Alkene isomerisation; Claisen reaction; High throughput screening; Ruthenium catalysts; Terpenoids; Unsaturated aldehydes

Indexed keywords

CESIUM; IMIDAZOLINE DERIVATIVE; MENTHONE; MYRTENAL; RUTHENIUM DERIVATIVE; SESQUITERPENOID; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CLAISEN REARRANGEMENT; TANDEM ISOMERIZATION;

EID: 20044362045     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404391     Document Type: Article

References (42)

1. L. Claisen, Ber. Dtsch. Chem. Ges. 1912, 45, 3157.
2. F. E. Ziegler, Chem. Rev. 1988, 88, 1423;
3. th edn., Vol. E21d, Thieme Verlag, Stuttgart, 1995, p. 3301.
4. C. J. Burrows, B. K. Carpenter, J. Am. Chem. Soc. 1981, 103, 6983;
5. D. E. Vogel, G. H. Büchi, Org. Synth. 1987, 66, 29;
6. R. E. Ireland, D. J. Dawson, Org. Synth. Col. Vol. VI 1988, 298;
7. J. S. Swenton, D. Bradin, B. D. Gates, J. Org. Chem. 1991, 56, 6156;
8. M. Sugiura, M. Yanagisawa, T. Nakai, Synlett 1995, 447.
9. H. Suzuki, Y. Koyama, Tetrahedron Lett. 1979, 20, 1415;
10. H. Wakamatsu, M. Nishida, N. Adachi, M. Mori, J. Org. Chem. 2000, 65, 3966;
11. S. Krompiec, M. Pigulla, W. Szczepankiewicz, T. Bieg, N. Kuznik, K. Leszczynska-Sedja, M. Kubichi, T. Borowiak, Tetrahedron Lett. 2001, 42, 7095.
12. A. Salvini, P. Frediani, F. Piacenti, J. Mol. Catal. A: Chemical 2000, 159, 185;
13. A. Salvini, F. Piacenti, P. Frediani, A. Devescovi, M. Caporali, J. Organomet. Chem. 2001, 625, 255;
14. K. Dallmann, R. Buffon, J. Mol. Catal. A: Chemical 2002, 185, 187;
15. K. Dallmann, R. Buffon, J. Mol. Catal. A: Chemical 2001, 172, 81.
16. R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345;
17. K. Tani, T. Yamagata, S. Otsuka, S. Akutagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori, J. Chem. Soc. Chem. Commun. 1982, 600;
18. K. Tani, T. Yamagata, S. Akutagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori, S. Otsuka, J. Am. Chem. Soc. 1984, 106, 5208;
19. H. Frauenrath, M. Kaulard, Synlett 1994, 517.
20. C. Cadot, P. I. Dalko, J. Cossy, Tetrahedron Lett. 2002, 43, 1839;
21. D. Bourgeois, A. Pancrazi, S. P. Nolan, J. Prunet, J. Organomet. Chem. 2002, 643-644, 247;
22. A. E. Sutton, B. A. Seigal, D. F. Finnegan, M. L. Snapper, J. Am. Chem. Soc. 2002, 124, 13390.
23. B. Schmidt, H. Wildemann, J. Org. Chem. 2000, 65, 5817;
24. B. Schmidt, Synlett 2004, 1541;
25. B. Schmidt, Eur. J. Org. Chem. 2004, 1865;
26. B. Alcaide, P. Almendros, Chem. Eur. J. 2003, 9, 1259.
27. J. M. Reuter, R. G. Salomon, J. Org. Chem. 1977, 42, 3360;
28. R. S. Iyer, M. E. Kobierski, R. G. Salomon, J. Org. Chem. 1994, 59, 6038;
29. T. N. Mitchell, F. Giesselmann, Synlett 1996, 475.
30. J. S. Swenton, D. Bradin, B. D. Gates, J. Org. Chem. 1991, 56, 6156;
31. T. Higashino, S. Sakaguchi, Y. Ishii, Org. Lett. 2000, 2, 4193;
32. S. G. Nelson, C. J. Bungard, K. Wang, J. Am. Chem. Soc. 2003, 125, 13000.
33. S. P. Miller, J. P. Morken, Org. Lett. 2002, 4, 2743.
34. D. Sémeril, M. Cléran, C. Bruneau, P. H. Dixneuf, Adv. Synth. Catal. 2001, 343, 184.
35. D. Sémeril, M. Cléran, A. Jimenez-Perez, C. Bruneau, P. H. Dixneuf, J. Mol. Catal. A: Chemical 2002, 9.
36. D. Sémeril, C. Bruneau, P. H. Dixneuf, Helv. Chim. Acta 2001, 84, 3335.
37. J. Le Nôtre, L. Brissieux, D. Sémeril, C. Bruneau, P. H. Dixneuf, Chem. Commun. 2002, 1772.
38. H. Ben Ammar, J. Le Nôtre, M. Salem, M. T. Kaddachi, P. H. Dixneuf, J. Organomet. Chem. 2002, 662, 63.
39. H. Ben Ammar, J. Le Nôtre, M. Salem, M. T. Kaddachi, L. Toupet, J.-L. Renaud, C. Bruneau, P. H. Dixneuf, Eur. J. Inorg. Chem. 2003, 4055.
40. J. Le Nôtre, C. Bruneau, P. H. Dixneuf, Eur J. Org. Chem. 2002, 3816;
41. J. Le Nôtre, A. Acosta Martinez, P. H. Dixneuf, C. Bruneau, Tetrahedron 2003, 59, 9425.
42. K. Peterfy, M. A. Garcia-Garibay, J. Am. Chem. Soc. 1998, 120, 4540.