Allylic etherification via Ir(I)/Zn(II) bimetallic catalysis

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2679-2682

  Roberts, Justin P ^a   Lee, Chulbom ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 29844450747     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0508328     Document Type: Article

References (46)

1. For reviews on bimetallic and bifunctional catalyses, see: (a) van Den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54, 12985.
2. (b) Rowlands, G. J. Tetrahedron 2001, 57, 1865.
3. (a) Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309.
4. (b) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
5. (c) Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230.
6. (d) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764.
7. (e) Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758.
8. (a) Evans, P. A.; Leahy, D. K. J. Am. Chem. Soc. 2002, 124, 7882.
9. (b) Evans, P. A.; Leahy, D. K.; Slieker, L. M. Tetrahedron: Asymmetry 2003, 14, 3613.
10. (a) Kim, H.; Lee, C. Org. Lett. 2002, 4, 4369.
11. (b) Kim, H.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 5, 1336.
12. (a) Evans, P. A.; Leahy, D. K.; Andrews, W. J.; Uraguchi, D. Angew. Chem., Int. Ed. 2004, 43, 4788.
13. (b) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794.
14. For the compatibility of zinc alkoxides with iridium catalyses, see: (a) Miyabe, H.; Matsumura, A.; Moriyama, K.; Takemoto, Y. Org. Lett. 2004, 6, 4631.
15. (b) Miyabe, H.; Yoshida, K.; Yamauchi, M.; Takemot, Y. J. Org. Chem. 2005, 70, 2148.
16. Ref 5b.
17. Parkin, G. Chem. Commun. 2000, 1971.
18. (a) Takeuchi, R.; Kashio, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 263.
19. (b) Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647.
20. (c) Janssen, J. P.; Helmchen, G. Tetrahedron Lett. 1997, 38, 8025.
21. For recent examples of carbon-heteroatom bond formation by Ir-catalyzed allylic alkylations, see: (a) Takeuchi, R.; Ue, N.; Tanabe, K.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525.
22. (b) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164.
23. (c) Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
24. (d) Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272.
25. (e) Miyabe, H.; Yoshida, K.; Matsumura, A.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 567.
26. (f) Miyabe, H.; Matsumura, A.; Yoshida, K.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 2123.
27. (g) Lipowski, G.; Helmchen, G. Chem. Commun. 2004, 116.
28. (h) Welter, C.; Kock, O.; Liposwky, G.; Helmchen, G. Chem. Commun. 2004, 896.
29. (i) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628.
30. (j) Miyabe, H.; Matsumura, A.; Moriyama, K.; Takemoto, Y. Org. Lett. 2004, 6, 4631.
31. For the use of a pybox-type ligand in the Ir-catalyzed allylic alkylation, see: (a) Lavastre, O.; Morken, J. P. Angew. Chem., Int. Ed. 1999, 38, 3163.
32. (b) Ref 9j.
33. (a) Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364.
34. 3- allyliridium complex, see: Bartels, B.; Garcia-Yebra, C.; Rominger, F.; Helmchen, G. Eur. J. Inorg. Chem. 2002, 2569.
35. For a chiral dialkene ligand in an Ir-catalyzed reaction, see ref 9i.
36. For a review, see: (a) Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 1, 26.
37. (b) For an example of profound halide effects on the regioselectivity in a Rh-catalyzed allylic etherification, see ref 3.
38. Parkin, G. Chem. Rev. 2004, 104, 699.
39. (a) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806.
40. (b) Frantz, D. E.; Fassler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373.
41. Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581.
42. (a) For discussion on an irido-enyl species, see ref 11b.
43. 3-allyl intermediate was utilized for asymmetric induction via deracemization.
44. See: (b) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
45. (a) Tobe, M. L. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: New York, 1987; Vol. 1, pp 281-329.
46. (b) Also see ref 12a.