Rhodium-catalyzed C-H amination: Versatile methodology for the selective preparation of amines and amine derivatives

Chemtracts

Volumn 18, Issue 1, 2005, Pages 1-13

  Du Bois, Justin ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBAMIC ACID DERIVATIVE; RHODIUM;

AMINATION; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL BOND; CHIRALITY; OXIDATION; REACTION ANALYSIS; REVIEW; RING OPENING; STEREOSPECIFICITY;

EID: 24744437771     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (52)

1. Goldman, A.S., Goldberg, K.I. In Activation and Functionalization of C-H Bonds, Goldberg, K.I., Goldman, A.S., eds., ACS Symposium Series, 885, 2004, pp. 1-43;
2. Davies, H.M.L., Beckwith, R.E.J. Chem. Rev. 2003, 103, 2861;
3. Kakiuchi, F., Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
4. Crabtree, R.H. J. Organomet. Chem. 2004, 689, 4083;
5. Labinger, J.A., Bercaw, J.E. Nature 2002, 417, 507.
6. For some recent examples, see: Wender, P.A., Hilinski, M.K., Mayweg, A.V.W. Org. Lett. 2005, 7, 79;
7. Hinman, A., Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510;
8. Kurosawa, W., Kan, T., Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 8112;
9. White, J.D., Hrnciar, P., Stappenbeck, F. J. Org. Chem. 1999, 64, 7871;
10. Taber, D.F., Stiriba, S.-E. Chem. Eur. J. 1998, 4, 990.
11. For recent comprehensive reviews, see: Dauban, P., Dodd, R.H. Synlett 2003, 1571;
12. Müller, P., Fruit, C. Chem. Rev. 2003, 103, 2905;
13. Müller, P. Transition Metal-Catalyzed Nitrene Transfer: Aziridination and Insertion, JAI Press Inc.: Greenwich, 1997, Vol. 2, pp. 113-151.
14. Abramovitch, R.A., Bailey, T.D., Takaya, T., Uma, V. J. Org. Chem. 1974, 39, 340.
15. Yamada, Y., Yamamoto, T., Okawara, M. Chem. Lett. 1975, 361.
16. Breslow, R., Gellman, S.H. J. Chem. Soc. Chem. Comm. 1982, 1400.
17. Breslow, R., Gellman, S.H. J. Am. Chem. Soc. 1983, 105, 6728.
18. Nägeli, I., Baud, C., Bernardinelli, G., Jacquier, Y., Moran, M., Müller, P. Helv. Chim. Acta 1997, 80, 1087;
19. Müller, P., Baud, C., Jacquier, Y., Moran, M., Nägeli, I. J. Phys. Org. Chem. 1996, 9, 341.
20. Mansuy, D., Mahy, J.-P., Dureault, A., Bedi, G., Battioni, P. J. Chem. Soc. Chem. Comm. 1984, 1161.
21. Carbamates were also chosen in place of carboxamides to avoid potential problems with Hofmann rearrangement. See: Zhang, L.-h., Kauffman, G.S., Pesti, J.A., Yin, J. J. Org. Chem. 1997, 62, 6918;
22. Mendre, C., Pascal, R., Calas, B. Tetrahedron Lett. 1994, 35, 5429;
23. Moriarty, R.M., Chany II, C.J., Vaid, R.K., Prakash, O., Tuladhar, S.M. J. Org. Chem. 1993, 58, 2478.
24. 2. See: Yu, X.-Q., Huang, J.-S., Zhou, X.-G., Che, C.-M. Org. Lett. 2000, 2, 2233.
25. Espino, C.G., Du Bois, J. Angew. Chem. Int. Ed. 2001, 40, 598.
26. Doyle, M.P., Ren, T. Prog. Inorg. Chem. 2001, 49, 113, and references therein.
27. Espino, C.G., Wehn, P.M., Chow, J., Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
28. Maryanoff, B.E., Costanzo, M.J., Nortey, S.O., et al. J. Med. Chem. 1998, 41, 1315;
29. Gritsonie, P., Pilkington, M., Wallis, J.D., Povey, D.C. Acta Cryst. 1994, C50, 763.
30. Wehn, P.M., Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950.
31. Parker, K.A., Chang, W. Org. Lett. 2003, 5, 3891.
32. Wehn, P.M., Lee, J., Du Bois, J. Org. Lett. 2003, 5, 4823.
33. Espino, C.G. Ph.D. Thesis, Stanford University, Stanford, CA, 2004.
34. Espino, C.G., Fiori, K.W., Kim, M., Brodsky, B.H., Du Bois, J. Manuscript in preparation.
35. Doyle, M.P., McKervey, M.A., Ye, T. Modern Catalytic Methods for Organic Synthesis With Diazo Compounds: From Cyclopropanes to Ylides, Wiley: New York, 1998.
36. Fiori, K.W., Fleming, J.J., Du Bois, J. Angew. Chem. Int. Ed. 2004, 43, 4349.
37. Fleming, J.J., Fiori, K.W., Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028.
38. Meléndez, R.E., Lubell, W.D. Tetrahedron 2003, 59, 2581.
39. Nakamura, E., Yoshikai, N., Yamanaka, M. J. Am. Chem. Soc. 2002, 124, 7181;
40. Sheehan, S.M., Padwa, A., Snyder, J.P. Tetrahedron Lett. 1998, 39, 949.
41. Simakov, P.A., Choi, S.-Y., Newcomb, M. Tetrahedron Lett. 1998, 39, 8187;
42. Du, X., Houk, K.N. J. Org. Chem. 1998, 63, 6480;
43. Yang, D., Wong, M.-K., Wang, X.-C., Tang, Y.-C. J. Am. Chem. Soc. 1998, 120, 6611.
44. Taber, D.F., Meagley, R.P., Louey, J.P., Rheingold, A.L. Inorg. Chim. Acta 1995, 239, 25.
45. Davies, H.M.L., Venkataramani, C. Org. Lett. 2003, 5, 1403;
46. Davies, H.M.L. Eur. J. Org. Chem. 1999, 2459.
47. Espino, C.G., Fiori, K.W., Kim, M., Du Bois, J. J. Am. Chem. Soc. 2004, 116, 15 378.
48. Fiori, K.W., Kim, M., Du Bois, J. Manuscript in preparation.
49. Padwa, A., Flick, A.C., Leverett, C.A., Stengel, T. J. Org. Chem. 2004, 69, 6377;
50. Huang, H., Panek, J.S. Org. Lett. 2003, 5, 1991;
51. Trost, B.M., Gunzner, J.L., Dirat, O., Rhee, Y.H. J. Am. Chem. Soc. 2002, 124, 10396;
52. Levites-Agababa, E., Menhaji, E., Perlson, L.N., Rojas, C.M. Org. Lett. 2002, 4, 863.