"Orthogonal" Lewis Acids: Catalyzed Ring Opening and Rearrangement of Acylaziridines

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4568-4569

  Ferraris, Dana ^a   Drury III, William J ^a   Cox, Christopher ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001009177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980558d     Document Type: Article

References (28)

1. Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. J. Am. Chem. Soc. 1996, 118, 5332.
2. Nishiguchi, T.; Tochio, H.; Nabeya, A.; Iwakura, Y. J. Am. Chem. Soc. 1969, 91, 5835.
3. (a) Lygo, B. Tetrahedron Lett. 1994, 35, 5073.
4. (b) Legters, J.; Willem, J. G. H.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 59.
5. a using Pearson's HSAB theory as a useful guideline. See: Huheey, J. E. Inorganic Chemistry; Harper and Row: New York, 1983; pp 312-315.
6. (a) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889.
7. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2743.
8. (c) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
9. (d) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
10. (e) Evans, D. A.; Margaret, M. F.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744.
11. For a general review of aziridine chemistry, see: Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol 1a.
12. (a) Hassner, A.; Matthews, G. J.; Fowler, F. W. J. Am. Chem. Soc. 1969, 91, 5046.
13. (b) Fowler, F. W.; Hassner, A.; Levy, L. A. J. Am. Chem. Soc. 1967, 89, 2077.
14. Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602.
15. The Hammett correlation gave a ρ value of 2.4; see the Supporting Information for the plot. For a discussion of Hammett correlations and tabular σ values, see: Advanced Organic Chemistry; March, J., Ed.; Wiley: New York; 1992; pp 278-286.
16. Olah, G. A.; Szilagyi, P. J. J. Am. Chem. Soc. 1969, 91, 2949.
17. Cho, S. J.; Cui, C.; Lee, J. Y.; Park, J. K.; Suh, S. B.; Park, J.; Kim, B. H.; Kim, K. S. J. Org. Chem. 1997, 62, 4068.
18. Olah, G. A.; Calin, M. J. Am. Chem. Soc. 1968, 90, 401.
19. w = 0.1811, GOF = 1.034.
20. Ohwada, T.; Achiwa, T.; Okamoto, I.; Shudo, K.; Yamaguchi, K. Tetrahedron Lett. 1998, 865.
21. These compounds are assigned cis stereochemistry on the basis of spectral similarity between 3b and material generated by known literature methods. All new oxazolines have been assigned a similar stereochemistry on the basis of analogy: Winstein, S.; Boschan, R. J. Am. Chem. Soc: 1950, 72, 2, 4669.
22. The Hammett plot gave a ρ value of -2.0. See the Supporting Information for the plot.
23. Heine, H. W.; Proctor, Z. J. Org. Chem. 1958, 23, 1554.
24. a and O.
25. Lithium cations are known to catalyze the N-acylaziridine to oxazoline rearrangment: Tanner, D.; Tedenborg, L.; Almario, A.; Pettersson, I.; Csöregh, I.; Kelly, N. M.; Andersson, P. G.; Högberg, T. Tetrahedron 1997, 53, 4857.
26. Nabeya, A.; Shigemoto, T.; Iwakura, Y. J. Org. Chem. 1975, 40, 3536.
27. (a) Akhmedzhanova, V. I.; Batsuren, D.; Shakirov, R. S. Chem. Nat. Cmpds. 1993, 29, 778.
28. (b) Myers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991.