An olefin metathesis/double bond isomerization sequence catalyzed by an in situ generated ruthenium hydride species

European Journal of Organic Chemistry

Volumn , Issue 5, 2003, Pages 816-819

  Schmidt, Bernd ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Homogeneous catalysis; Isomerization; Metathesis; Oxacycles; Rearrangement

Indexed keywords

ALKENE; RUTHENIUM DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; ISOMERISM; MIGRATION;

EID: 0037337709     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390124     Document Type: Article

References (54)

1. [1a] A. de Meijere, S. Bräse, J. Organomet. Chem. 1999, 576, 88-110.
2. [1b] R. Grigg, V. Sridharan, J. Organomet. Chem. 1999, 576, 65-87.
3. [1c] L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
4. [2a] S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
5. [2b] R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450.
6. [2c] M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
7. [2c] M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
8. [2d] A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3013-3043.
9. [2d] A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3013-3043.
10. [3a] R. Stragies, S. Blechert, Synlett 1998, 169-170.
11. [3b] R. Stragies, S. Blechert, J. Am. Chem. Soc. 2000, 122, 9584-9591.
12. [3c] A. Rückert, D. Eisele, S. Blechert, Tetrahedron Lett. 2001, 42, 5245- 5247.
13. [4a] J. Louie, C. W. Bielawski, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 11312-11313.
14. [4b] S. D. Drouin, F. Zamanian, D. E. Fogg, Organometallics 2001, 20, 5495-5497.
15. [5a] P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110.
16. [5b] M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956.
17. [6a] T. E. Wilhelm, T. R. Belderrain, S. N. Brown, R. H. Grubbs, Organometallics 1997, 16, 3867-3869.
18. [6b] S. D. Drouin, G. P. A. Yap, D. E. Fogg, Inorg. Chem. 2000, 39, 5412-5414.
19. [6c] J. Wolf, W. Stüer, C. Grünwald, H. Werner, P. Schwab, M. Schulz, Angew. Chem. 1998, 110, 1165-1167; Angew. Chem. Int. Ed. 1998, 110, 1124-1126.
20. [6c] J. Wolf, W. Stüer, C. Grünwald, H. Werner, P. Schwab, M. Schulz, Angew. Chem. 1998, 110, 1165-1167; Angew. Chem. Int. Ed. 1998, 110, 1124-1126.
21. [6d] M. Olivan, K. G. Caulton, Inorg. Chem. 1999, 38, 566-570.
22. [7a] B. Schmidt, Org. Lett. 2000, 2, 791-794.
23. [7b] B. Schmidt, H. Wildemann, Eur. J. Org. Chem. 2000, 3145-3163.
24. [7c] B. Schmidt, H. Wildemann, J. Chem. Soc., Perkin Trans. 1 2000, 2916-2925.
25. [8a] R. E. Ireland, I. Armstrong, J. D. J. Lebreton, R. S. Meissner, M. A. Rizzacasa, J. Am. Chem. Soc. 1993, 115, 7152-7165.
26. [8b] S. J. Danishefsky, S. DeNinno, P. Lartey, J. Am. Chem. Soc. 1987, 109, 2082-2089.
27. [8c] P. J. Kocienski, R. C. D. Brown, A. Pommier, M. Procter, B. Schmidt, J. Chem. Soc., Perkin Trans. 1 1998, 9-39.
28. [8d] K. A. Parker, A. T. Georges, Org. Lett. 2000, 2, 497-499.
29. [8e] R. W. Friesen, R. W. Loo, C. F. Sturino, Can. J. Chem. 1994, 72, 1262-1272.
30. [9a] C. F. Sturino, J. C. Y. Wong, Tetrahedron Lett. 1998, 39, 9623-9626.
31. [9b] D. Calimente, M. H. D. Postema, J. Org. Chem. 1999, 64, 1770-1771.
32. [9c] D. R. Williams, G. S. Cortez, S. L. Bogen, C. M. Rojas, Angew. Chem. 2000, 112, 4750-4753; Angew. Chem. Int. Ed. 2000, 39, 4612-4615.
33. [9c] D. R. Williams, G. S. Cortez, S. L. Bogen, C. M. Rojas, Angew. Chem. 2000, 112, 4750-4753; Angew. Chem. Int. Ed. 2000, 39, 4612-4615.
34. [9d] J. M. Cox, J. D. Rainier, Org. Lett. 2001, 3, 2919-2922.
35. [9e] A. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783-3784.
36. H. Oguri, S. Tanaka, T. Oishi, M. Hirama, Tetrahedron Lett. 2000, 41, 975-978.
37. M. E. Maier, M. Bugl, Synlett 1998, 1390-1392.
38. P. V. Ramachandran, J. S. Chandra, M. V. R. Reddy, J. Org. Chem. 2002, 67, 7547-7550.
39. [13a] E. J. Corey, J. W. Suggs, J. Org. Chem. 1973, 38, 3224.
40. [13b] J. J. Oltvoort, C. A. A. van Boeckel, J. H. De Koning, J. H. van Boom, Synthesis 1981, 305-308.
41. [13c] A. Wille, S. Tomm, H. Frauenrath, Synthesis 1998, 305-308.
42. [13d] H. Frauenrath, T. Philips, Angew. Chem. 1986, 98, 261-262; Angew. Chem. Int. Ed. Engl. 1986, 25, 274-275.
43. [13d] H. Frauenrath, T. Philips, Angew. Chem. 1986, 98, 261-262; Angew. Chem. Int. Ed. Engl. 1986, 25, 274-275.
44. [13e] H. Brunner, M. Prommesberger, Tetrahedron: Asymmetry 1998, 9, 3231-3239.
45. [13f] J. Le Nôtre, L. Brissieux, D. Semeril, C. Bruneau, P. H. Dixneuf, Chem. Commun. 2002, 1772-1773.
46. P. J. Kocienski, Protecting Groups, Georg Thieme Verlag, Stuttgart, 1994.
47. H. Frauenrath, D. Brethauer, S. Reim, M. Maurer, G. Raabe, Angew. Chem. 2001, 113, 176-178; Angew. Chem. Int. Ed. 2001, 40, 177-179.
48. H. Frauenrath, D. Brethauer, S. Reim, M. Maurer, G. Raabe, Angew. Chem. 2001, 113, 176-178; Angew. Chem. Int. Ed. 2001, 40, 177-179.
49. H. Frauenrath, J. Runsink, J. Org. Chem. 1987, 52, 2707-2712.
50. [17a] D. Joe, L. E. Overman, Tetrahedron Lett. 1997, 38, 8635-8638.
51. [17b] T. R. Hoye, H. Zhao, Org. Lett. 1999, 1, 1123-1125.
52. [17c] A. Fürstner, O. R. Thiel, L. Ackermann, H.-J. Schanz, S. P. Nolan, J. Org. Chem. 2000, 65, 2204-2207.
53. [17d] C. Cadot, P. I. Dalko, J. Cossy, Tetrahedron Lett. 2002, 43, 1839-1841.
54. A. E. Sutton, B. A. Seigal, D. F. Finnegan, M. L. Snapper, J. Am. Chem. Soc. 2002, 124, 13390-13391.