On the mechanism of a double ring-closing metathesis reaction

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 591-594

  Wallace, Debra J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Intermediates; Ring closing metathesis; Spirocycles

Indexed keywords

ALKENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; KINETICS; RING CLOSING METATHESIS;

EID: 11144263600     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.149     Document Type: Article

References (36)

1. D.J. Wallace, J.M. Goodman, D.J. Kennedy, A.J. Davies, C.J. Cowden, M.S. Ashwood, I.F. Cottrell, U.-H. Dolling, and P.J. Reider Org. Lett. 3 2001 671
2. D.J. Wallace, C.J. Cowden, D.J. Kennedy, M.S. Ashwood, I.F. Cottrell, and U.-H. Dolling Tetrahedron Lett. 41 2000 2027
3. For other synthetic approaches to this molecule see: J.J. Kulagowski, N.R. Curtis, C.J. Swain, and B.J. Williams Org. Lett. 3 2001 667
4. P.E. Maligres, M.M. Waters, J. Lee, R.A. Reamer, D. Askin, M.S. Ashwood, and M. Cameron J. Org. Chem. 67 2002 1093
5. C.E. Raab, D.C. Dean, and D.G. Melillo J. Labelled Compd. Radiopharm. 44 2001 815
6. For recent reviews of RCM reactions see: M.L. Snapper A.H. Hoveyda Tetrahedron symposium in print 55 1999 8141
7. A. Furstner Alkene Metathesis in Organic Synthesis Top. Organomet. Chem. 1 1998
8. S. Blechert Pure Appl. Chem. 8 1999 1393
9. A. Furstner Angew. Chem., Int. Ed. 39 2000 3012
10. T.M. Trnka, and R.H. Grubbs Acc. Chem. Res. 34 2001 18
11. R.E. Schrock, and A.H. Hoveyda Angew. Chem., Int. Ed. 42 2003 4592
12. M.A. Walters Prog. Heterocycl. Chem. 15 2003 1
13. A. Deiters, and S.F. Martin Chem. Rev. 104 2004 2199
14. For formation of spirocyclic compounds via multiple RCM reactions see: M.J. Bassindale, P. Hamley, A. Leitner, and J.P.A. Harrity Tetrahedron Lett. 40 1999 3247
15. B. Schmidt, and M. Westhus Tetrahedron 56 2000 2421
16. B. Schmidt, and H. Wildemann J. Org. Chem. 65 2000 5817
17. B. Schmidt, and H. Wildemann J. Chem. Soc., Perkin Trans. 1 2000 2916
18. D.J. Wallace, P.G. Bulger, D.J. Kennedy, M.S. Ashwood, I.F. Cottrell, and U.-H. Dolling Synlett 2001 357
19. M.-P. Heck, C. Baylon, S.P. Nolan, and C. Mioskowski Org. Lett. 3 2001 1989
20. R.A.J. Wybrow, L.A. Johnson, B. Auffray, W.J. Moran, H. Adams, and J.P.A. Harrity Tetrahedron Lett. 43 2002 7851
21. A.S. Edwards, R.A. Wybrow, C. Johnson, H. Adams, and J.P.A. Harrity Chem. Commun. 2002 1542
22. D.J. Wallace Tetrahedron Lett. 44 2003 2145
23. R.A.J. Wybrow, N.G. Stevenson, and J.P.A. Harrity Synlett 2004 140
24. R.A.J. Wybrow, A.S. Edwards, N.G. Stevenson, H. Adams, C. Johnstone, and J.P.A. Harrity Tetrahedron 60 2004 8869
25. P. Schwab, R.H. Grubbs, and J.W. Ziller J. Am. Chem. Soc. 118 1996 100
26. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
27. S.B. Garber, J.S. Kingsbury, B.L. Gray, and A.H. Hoveyda J. Am. Chem. Soc. 122 2000 8168
28. S. Gessler, S. Randl, and S. Blechert Tetrahedron Lett. 41 2000 9973
29. J.S. Kingsbury, J.P.A. Harrity, P.J. Bonitatebus Jr., and A.H. Hoveyda J. Am. Chem. Soc. 121 1999 791
30. Reactions were run in 0.1 M dichloromethane at room temperature using 5 mol % catalyst, additional catalyst was sometimes added
31. A different ratio of intermediates was observed when the reaction was carried out using the original solvent of chloroform
32. 3S (M+H) 396.1633, found 396.1635
33. In this letter we use the term 'first generation catalyst' to cover those laking the dihydroimidazole ligand, that is, 4 and 7 and 'second generation catalyst' to cover those with the dihydroimidazole ligand, that is, 5 and 6
34. M. Ulman, and R.H. Grubbs Organometallics 17 1998 2484
35. T.R. Hoye, and H. Zhao Org. Lett. 1 1999 1123
36. The stereochemical outcome of this reaction was determined by conversion of the mixtures of 14a and b, or 15a and b to the known compounds 8 and 9