Ruthenium-catalyzed yne-ene cross metathesis binding to solid support and cleavage by Pd0-catalysis

Synlett

Volumn , Issue 2, 1998, Pages 166-168

  Schürer, Stephan C ^a   Blechert, Siegfried ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001540138     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1591     Document Type: Article

References (35)

1. For recent reviews see: (a) Blechert, S.; Schuster, M. Angew. Chem. 1997, 109, 2124;
2. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
3. (b) Hashmi, A. S. K. J. Prakt. Chem. 1997, 339, 195.
4. (c) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
5. Examples for selective cross metathesis: (a) Gibson, S. E.; Gibson, V. C.; Keen, S. P. Chem. Commun. 1997, 1107.
6. (b) Barrett, A. G. M.; Baugh, S. P. D.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A. Chem. Comun. 1997, 155.
7. (c) Brümmer, O.; Rückert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441.
8. (d) Feng, J.; Schuster, M.; Blechert, S. Synlett 1997, 129.
9. (e) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117.
10. For recent reviews see e.g.: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. 1996, 108, 2436;
11. Angew. Chem., In. Ed. Engl. 1996, 35, 2289.
12. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
13. For ruthenium carbene initiators see: Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179;
14. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
15. Schuster, M.; Lucas, N.; Blechert, S. Chem. Commun. 1997, 823.
16. Stragies, R.; Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2628;
17. Angew. Chem., Int. Ed. Engl. 1997, 36, 2518.
18. Selected ruthenium-catalyzed enyne cyclizations: (a) Barrett, A. G. M.; Baugh, S. P. D.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A. Chem. Commun. 1997, 1375.
19. (b) Hammer, K.; Undheim, K. Tetrahedron 1997, 53, 10603.
20. Kinoshita, A.; Mori, M. Synlett 1994, 1020.
21. Examples for traceless linkers: (a) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006.
22. (b) Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999.
23. For reviews see e.g.: (a) Trost, B. M. Angew. Chem. 1989, 101, 1199;
24. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
25. (b) Tsuji, J. Tetrahedron 1986, 42, 4361.
26. Flegelová, Z.; Pátek, M. J. Org. Chem. 1996, 61, 6735.
27. 0-labile allyl linkers see: (a) Kaljuste, K.; Undén, A. Tetrahedron Lett. 1996, 37, 3031.
28. (b) Lloyd-Williams, P.; Merzouk, A.; Guibé, F.; Albericio, F.; Giralt, E. Tetrahedron Lett. 1994, 35, 4437.
29. (c) Lloyd-Williams, P.; Jou, G.; Albericio, F.; Giralt, E. Tetrahedron Lett. 1991, 52, 4207.
30. (d) Kunz, H.; Dombo, R. Angew. Chem. 1988, 100, 732;
31. Angew. Chem., Int. Ed. Engl. 1988, 27, 711.
32. 4Si m/z 284.144388, measured 284.1444.
33. For a review see: Sembner, G.; Parthier, B. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1993, 44, 569.
34. Blechert, S.; Bockelmann, C.; Brümmer, O.; Füβlein, M.; Gundlach, H.; Haider, G.; Hölder, S.; Kutchan, T. M.; Weiler, E. W.; Zenk, M. H. Perkin Trans. 1, in press.
35. For an example see: Tsuji, J.; Yamakawa, T. Tetrahedron Lett. 1979, 20, 613.