Dynamic kinetic asymmetric allylic amination and acyl migration of vinyl aziridines with imido carboxylates

Angewandte Chemie - International Edition

Volumn 46, Issue 32, 2007, Pages 6123-6125

  Trost, Barry M ^a   Fandrick, Daniel R ^a   Brodmann, Tobias ^a   Stiles, Dylan T ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Balanol; Homogeneous catalysis; Palladium; Vinyl aziridines

Indexed keywords

AMINATION; CHIRALITY; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; BALANOL; HOMOGENEOUS CATALYSIS; VINYL AZIRIDINES;

VINYL RESINS;

ALLYL COMPOUND; AZIRIDINE DERIVATIVE; CARBOXYLIC ACID; VINYL DERIVATIVE;

ACYLATION; AMINATION; ARTICLE; CHEMISTRY; KINETICS;

ACYLATION; ALLYL COMPOUNDS; AMINATION; AZIRIDINES; CARBOXYLIC ACIDS; KINETICS; VINYL COMPOUNDS;

EID: 34548083986     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700835     Document Type: Article

References (33)

1. a) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364;
2. b) B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2944;
3. c) B. M. Trost, J. Org. Chem. 2004, 69, 5813-5837.
4. a) B. M. Trost, E. J. McEachern, F. D. Toste, J. Am. Chem. Soc. 1998, 120, 12 702-12 703;
5. b) B. M. Trost, T. L. Calkins, C. Oertelt, J. Zambrano, Tetrahedron Lett. 1998, 39, 1713-1716L;
6. c) B. M. Trost, C. Jiang, J. Am. Chem. Soc. 2001, 123, 12 907-12 908.
7. a) B. M. Trost, D. R. Fandrick, J. Am. Chem. Soc. 2003, 125, 11 836-11 837;
8. b) C. Dong, H. Alper, Tetrahedron: Asymmetry 2004, 15, 1537-1540;
9. c) B. M. Trost, D. R. Fandrick, Org. Lett. 2005, 7, 823-826.
10. D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772;
11. Angew. Chem. Int. Ed. 1998, 37, 2580-2627.
12. a) B. M. Trost, Science 1991, 254, 1471-1477;
13. b) B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705.
14. B. M. Trost, R. C. Bunt, R. C. Lemoine, T. L. Calkins, J. Am. Chem. Soc. 2000, 122, 5968-5976.
15. a) Y. Ohfune, N. Kurokawa, Tetrahedron Lett. 1984, 25, 1071-1074;
16. b) D. B. Berkowitz, G. Maiti, Org. Lett. 2004, 6, 2661-2664.
17. The lower yields of the desired products reported in Table 2 compared to those in Table 1 may result from the formation of a small amount of a by-product that may be the cyclic urea derived from loss of the alkoxy group in the tetrahedral intermediate of the isomerization step.
18. a) P. Kulanthaivel, Y. F. Hallock, C. Boros, S. M. Hamilton, W. P. Janzen, L. M. Ballas, C. R. Loomis, J. B. Jiang, J. Katz, R. Steiner, J. Clardy, J. Am. Chem. Soc. 1993, 115, 6452-6453;
19. b) S. Ohshima, M. Yanagisawa, A. Katoh, T. Fujii, T. Sano, S. Matsukuma, T. Furumai, M. Fujiu, K. Watanabe, K. Yohose, M. Arisawa, T. Okude, J. Antibiot. 1994, 47, 639-647.
20. A. Deiters, S. F. Martin, Chem. Rev. 2004, 104, 2199-2238.
21. For recent efforts towards the synthesis of balanol see: a) G. R. Cook, P. S. Shanker, S. L. Peterson, Org. Lett. 1999, 1, 615-618;
22. b) A. Furstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742;
23. c) D. Riber, R. Hazell, T. Skrydstrup, J. Org. Chem. 2000, 65, 5382-5390;
24. d) C. E. Masse, A. J. Morgan, J. S. Panek, Org. Lett. 2000, 2, 2571-2573;
25. e) J. P. Genet, P. Phansavath, S. D. Paule, V. Ratovelomanana-Vidal, Eur. J. Org. Chem. 2000, 3903-3907;
26. f) J. S. Yadav, C. Srinivas, Tetrahedron Lett. 2002, 43, 3837-3839;
27. g) J. S. Yadav, C. Srinivas, Tetrahedron 2003, 59, 10 325-10 329;
28. h) S. Raghavan, C. N. Kumar, Tetrahedron Lett. 2006, 47, 1585-1588, and references therein.
29. a) H. C. Brown, K. A. Keblys, J. Am. Chem. Soc. 1964, 86, 1795-1801;
30. b) D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1988, 110, 6917-6918.
31. J. W. Lampe, P. F. Hughes, C. K. Biggers, S. H. Smith, H. Hu, J. Org. Chem. 1996, 61, 4572-4581.
32. H. Hu, S. Hollinshead, S. E. Hall, K. Kalter, L. M. Ballas, Bioorg. Med. Chem. Lett. 1996, 6, 973-978.
33. J. Boivin, B. Quiclet-Sire, L. Ramos, S. Z. Zard, Chem. Commun. 1997, 353-354.