Catalyst selection for metal carbene transformations

Journal of Organometallic Chemistry

Volumn 617-618, Issue , 2001, Pages 98-104

  Timmons, Daren J ^a   Doyle, Michael P ^a  

^a University of Arizona   (United States)

Author keywords

Asymmetric catalysis; Cyclopropanation; Diazo compound; Dirhodium(II) carboxamidates; Insertion; Metal carbene

Indexed keywords

EID: 0346882176     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00637-9     Document Type: Article

References (44)

1. Doyle M.P., McKervey M.A., Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides. 1998;Wiley, New York.
2. (a) M.P. Doyle, D.C. Forbes, Chem. Rev. 98 (1998) 911.
3. (b) M.P. Doyle, Enantiomer 4 (1999) 621.
4. (c) M.P. Doyle, M.N. Protopopova, Tetrahedron 54 (1998) 7917.
5. (a) A. Padwa, D.J. Austin, Angew. Chem. Int. Ed. Engl. 33 (1994) 1797.
6. (b) A. Padwa, K.E. Krumpe, Tetrahedron 48 (1992) 5385.
7. (a) T. Ye, M.A. McKervey, Chem. Rev. 94 (1994) 1091.
8. (b) M.P. Doyle, M.A. McKervey, J. Chem. Soc. Chem. Commun. (1997) 983.
9. Miller D.J., Moody C.J. Tetrahedron. 51:1995;10811.
10. Doyle M.P., Zhou Q.-L., Raab C.E., Roos G.H.P., Simonsen S.H., Lynch V. Inorg. Chem. 35:1996;6064.
11. M.P. Doyle, Q.-L. Zhou, S.H. Simonsen, V. Lynch, Synlett (1996) 697.
12. Doyle M.P., Davies S.B., Hu W. Org. Lett. 2:2000;1145.
13. M.P. Doyle, S.B. Davies, W. Hu, J. Chem. Soc. Chem. Commun. (2000) 867.
14. Cotton F.A., Walton R.A. Multiple Bonds between Metal Atoms. 2nd ed. 1993;431 Clarendon Press, Oxford.
15. Doyle M.P. Chapter 7. Adams R.D., Cotton F.A., Catalysis by Di- and Polynuclear Metal Cluster Complexes. 1998;VCH Publishers, New York.
16. Doyle M.P., Raab C.E., Roos G.H.P., Lynch V., Simonsen S.H. Inorg. Chim. Acta. 266:1997;13.
17. Doyle M.P., Winchester W.R., Hoorn J.A.A., Lynch V., Simonsen S.H., Ghosh R. J. Am. Chem. Soc. 115:1993;9968.
18. Doyle M.P., Winchester W.R., Protopopova M.N., Kazala A.P., Westrum L.J. Org. Synth. 73:1996;13.
19. Doyle M.P., Winchester W.R., Protopopova M.N., Müller P., Bernardinelli G., Ene D.G., Motallebi S. Helv. Chim. Acta. 76:1993;2227.
20. Doyle M.P., Dyatkin A.B., Protopopova M.N., Yang C.I., Miertschin C.S., Wincheseter W.R., Simonsen S.H., Lynch V., Ghosh R. Recueil Trav. Chim. Pays-Bas. 114:1995;5763.
21. Doyle M.P., Austin R.E., Bailey A.S., Dwyer M.P., Dyatkin A.B., Kalinin A.V., Kwan M.M.Y., Liras S., Oalmann C.J., Pieters R.J., Protopopova M.N., Raab C.E., Roos G.H.P., Zhou Q.-L., Martin S.F. J. Am. Chem. Soc. 117:1995;5763.
22. Doyle M.P., Winchester W.R., Simonsen S.H., Ghosh R. Inorg. Chim. Acta. 220:1994;193.
23. M.P. Doyle, Q.-L. Zhou, C. Charnsangavej, M.A. Longoria, Tetrahedron Lett. 37 (1996) 4129.
24. Doyle M.P., -L. Zhou Q., Dyatkin A.B., Ruppar D.A. Tetrahedron Lett. 36:1995;7579.
25. M.P. Doyle, C.S. Peterson, Q.-L. Zhou, H. Nishiyama, J. Chem. Soc. Chem. Commun. (1997) 211.
26. Doyle M.P., van Oeveren A., Westrum L.J., Protopopova M.N., Clayton T.W. Jr. J. Am. Chem. Soc. 113:1991;8982.
27. Bode J.W., Doyle M.P., Protopopova M.N., Zhou Q.-L. J. Org. Chem. 61:1996;9146.
28. Doyle M.P., Dyatkin A.B., Roos G.H.P., Canas F., Pierson D.A., van Basten A., Müller P., Polleux P. J. Am. Chem. Soc. 116:1994;4507.
29. Doyle M.P., Kalinin A.V., Ene D.G. J. Am. Chem. Soc. 118:1996;8837.
30. Doyle M.P., Tedrow J.S., Dyatkin A.B., Spaans C.J., Ene D.G. J. Org. Chem. 64:1999;8907.
31. Doyle M.P., Austin R.E., Bailey A.S., Dwyer M.P., Dyatkin A.B., Kalinin A.V., Kwan M.M.Y., Liras S., Oalmann C.J., Pieters R.J., Protopopova M.N., Raab C.E., Roos G.H.P., Zhou Q.-L., Martin S.F. J. Am. Chem. Soc. 117:1995;5763.
32. Davies H.W.L., Doan B.D. J. Org. Chem. 64:1999;8501.
33. For reviews of the effectiveness of chiral dirhodium(II) carboxylates with styryldiazoacetates in cyclopropanation reactions see: (a) H.M.L. Davies, Aldrichim. Acta (1997) 107. (b) H.M.L. Davies, Eur. J. Org. Chem. (1999) 2459.
34. For reviews of the effectiveness of chiral dirhodium(II) carboxylates with styryldiazoacetates in cyclopropanation reactions see: (a) H.M.L. Davies, Aldrichim. Acta (1997) 107. (b) H.M.L. Davies, Eur. J. Org. Chem. (1999) 2459.
35. Doyle M.P., Ene D.G., Peterson C.S., Lynch V. Angew. Chem. Int. Ed. Engl. 38:1999;700.
36. Doyle M.P., Hu W. Tetrahedron Lett. 41:2000;6265.
37. Doyle M.P., Forbes D.C., Vasbinder M.M., Peterson C.S. J. Am. Chem. Soc. 120:1998;7653.
38. Kitagaki S., Anada M., Kataoka O., Matsuno K., Umeda C., Watanabe N., Hashimoto S. J. Am. Chem. Soc. 121:1999;1417.
39. Fukuda T., Katsuki T. Tetrahedron Lett. 38:1997;3443.
40. Uchida T., Irie R., Katsuki T. Tetrahedron. 56:2000;3501.
41. Niimi T., Uchida T., Irie R., Katsuki T. Tetrahedron Lett. 41:2000;3647.
42. Nishiyama H., Itoh Y., Sugawara Y., Matsumoto H., Aoki K., Itoh K. Bull. Chem. Soc. Jpn. 68:1995;1247.
43. S. Kitagaki, H. Matsuda, N. Watanabe, S. Hashimoto, Synlett. (1997) 1171.
44. Müller P., Baud C., Ene D., Motallebi S., Doyle M.P., Brandes B.D., Dyatkin A.B., See M.M. Helv. Chim. Acta. 78:1995;459.