Unusual Selectivity of Unprotected Aziridines in Palladium-Catalyzed Allylic Amination Enables Facile Preparation of Branched Aziridines

Journal of the American Chemical Society

Volumn 126, Issue 16, 2004, Pages 5086-5087

  Watson, Iain D G ^a   Styler, Sarah A ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AZIRIDINE DERIVATIVE; PALLADIUM;

ALLYLIC REARRANGEMENT; AMINATION; ARTICLE; CATALYSIS; SYNTHESIS;

EID: 1942521263     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049242f     Document Type: Article

References (33)

1. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
2. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14.
3. (a) Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763.
4. (b) Ichikawa, Y.; Ito, T.; Nishiyama, T.; Isobe, M. Synlett 2003, 1034-1036.
5. (c) Ito, K.; Akashi, S.; Saito, B.; Katsuki, T. Synlett 2003, 1809-1812.
6. (d) Paquette, L. A.; Leit, S. M. J. Am. Chem. Soc. 1999, 121, 8126-8127.
7. (e) Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087-11110.
8. (f) Liu, H.; Liang, X.; Sohoel, H.; Buelow, A.; Bols, M. J. Am. Chem. Soc. 2001, 123, 5116-5117.
9. (g) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458.
10. (a) Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
11. (b) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708.
12. Trost, B. M.; VanVranken, D. L. Chem. Rev. 1996, 96, 395-422.
13. Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2003, 68, 5160-5167 and references therein.
14. (a) Sasaki, M.; Yudin, A. K. J. Am. Chem. Soc. 2003, 125, 14242-14243.
15. (b) Sasaki, M.; Dalili, S.; Yudin, A. K. J. Org. Chem. 2003, 68, 2045-2047.
16. (c) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531.
17. Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247-258. Watson, I. D. G.; Yudin, A. K. Curr. Opin. Drug Discovery Dev. 2002, 5, 906-917.
18. Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247-258. Watson, I. D. G.; Yudin, A. K. Curr. Opin. Drug Discovery Dev. 2002, 5, 906-917.
19. (a) Alezra, V.; Bouchet, C.; Micouin, L.; Bonin, M.; Husson, H.-P. Tetrahedron Lett. 2000, 41, 655-658.
20. (b) Alezra, V.; Bonin, M.; Micouin, L.; Policar, C.; Husson, H.-P. Eur. J. Org. Chem. 2001, 2589-2594.
21. (a) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471-7472.
22. (b) Hayashi, T.; Kishi, K.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1990, 31, 1743-1746.
23. (a) Trost, B. M.; Keinan, E. J. Org. Chem. 1979, 44, 3451-3457.
24. (b) Akermark, B.; Vitagliano, A. Organometallics 1985, 4, 1275-1283.
25. (c) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165-2166.
26. (d) Murahashi, S.-I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303.
27. (e) Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem. 1994, 59, 4007-4009.
28. 4 in THF at 60 °C gives full conversion to the background products in 6 h.
29. Keinan, E.; Kumar, S.; Dangur, V.; Vaya, J. J. Am. Chem. Soc. 1994, 116, 11151-11152.
30. Recently, an exception for cinnamyl acetate was noted by Hartwig et al. in the iridium system: (a) Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272-14273.
31. (b) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165.
32. (a) Lee, W. K.; Ha, H.-J. Aldrichimica Acta 2003, 36, 57-63.
33. (b) Cardillo, G.; Gentilucci, L.; Tolomelli, A. Aldrichimica Acta 2003, 36, 39-50.