Oxidative Cycloamination of Olefins with Aziridines as a Versatile Route to Saturated Nitrogen-Containing Heterocycles

Journal of the American Chemical Society

Volumn 125, Issue 47, 2003, Pages 14242-14243

  Sasaki, Mikio ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AZIRIDINE DERIVATIVE; NITROGEN;

ADDITION REACTION; AMINATION; ARTICLE; BIOAVAILABILITY; BIOSYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; EPOXIDATION; MOLECULAR INTERACTION; OXIDATION; OXIDATIVE STRESS; RING OPENING; THERMODYNAMICS; THIN LAYER CHROMATOGRAPHY; X RAY ANALYSIS;

EID: 0344443388     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037726q     Document Type: Article

References (28)

1. Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
2. (a) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530.
3. (b) Caiazzo, A.; Dalili, S.; Yudin, A. K. Org. Lett. 2002, 4, 2597,
4. (c) Sasaki, M.; Dalili, S.; Yudin, A. K. J. Org. Chem. 2003, 68, 2045.
5. (d) Watson, I. D. G.; Yudin, A. K. Curr. Opin. Drug Discovery Dev. 2002, 5, 906.
6. For use of aziridines in complex molecule synthesis, see: Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
7. For a one-electron process, the 0.8 V anodic shift corresponds to the 18 kcal/mol increase in oxidative stability.
8. Iminium ions are known to form during secondary amine oxidation processes: Gilchrist, T. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 735.
9. See Supporting Information for experimental details.
10. Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: London. 1985.
11. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
12. For example, see: (a) Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach; Wiley & Sons: Chichester, U.K., 1997; Chapter 6.
13. (b) Hagan, D. O. Nat. Prod. Rep. 2000, 17, 435.
14. For reviews, see: (a) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862 and references therein.
15. (b) Pichon, M: Figadere, B. Tetrahedron: Asymmetry. 1996, 7, 927 and references therein.
16. (c) Higasio, Y.; Shoji, T. Appl. Catal., A 2001, 221, 197.
17. For the synthesis of [5, 3] bicyclic aziridines, see: (d) Coleman, R. S. ; Kong, J.-S.; Richardson, T. E. J. Am. Chem. Soc. 1999, 121, 9088.
18. (e) Mulzer, J.; Becker, R.; Brunner, E. J. Am. Chem. Soc. 1989, 111, 7500.
19. (f) Guillemin, J. C.; Denis, J. M. Angew. Chem. 1982, 94, 715.
20. (g) Chaabouni, R.; Laurent, A.; Marquet, B. Tetrahedron 1980, 36, 877.
21. Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53. 5491.
22. We were able to isolate and characterize the N-Cl-containing intermediate. See Supporting Information.
23. (a) Nagaoka, K.; Matsumoto, M.; Ono. J.; Yokoi, K.; Ishizeki, S.; Nakashima, T. J, Antibiot. 1986, 39. 1527.
24. (b) Coleman, R. S.; Li, J.; Navarro, A. Angew. Chem. Int. Ed. 2001, 40, 1736.
25. Tallent, W. H.; Horning, E. C. J. Am. Chem. Soc. 1956, 78, 4467.
26. For highly enantioselective Julia-Colonna epoxidation followed by conversion into aziridine, see: (a) Nemoto, T.; Ohshima, T.; Shibasaki, M. Yuki Gosei Kagaku Kyokaishi 2002, 60, 94 and references therein.
27. For ring opening by azide and reductive ring closing to aziridine, see: (b) Jin, X. L.; Sugihara, H.; Daikai, K.; Tateishi, H.; Jin, Y. Z.; Furuno, H.; Inanaga, J. Tetrahedron 2002, 58, 8321-8329.
28. (c) Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 4881-4.