Formation of a carbon-nitrogen bond via a 5-exo-trig radical cyclization onto the nitrogen of an imidate ester

Tetrahedron

Volumn 54, Issue 25, 1998, Pages 7121-7126

  McClure, Cynthia K ^a   Kiessling, Anthony J ^a,b   Link, Jeffrey S ^a  

^a MONTANA STATE UNIVERSITY   (United States)

^b WILKES UNIVERSITY   (United States)

Author keywords

Imidic acid esters; Radical cyclization

Indexed keywords

ALKALOID; ESTER;

ARTICLE; CHEMICAL BOND; CYCLIZATION; PRIORITY JOURNAL;

EID: 0032543733     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00351-2     Document Type: Article

References (30)

1. (3) (a) Curran, D. P.; Porter, N. A.; Giese, B., Eds.; Stereochemistry of Radical Reactions: Concepts, Guidelines and Synthetic Applications; VCH: New York, 1996.
2. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 4, pp. 779-831.
3. (c) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986.
4. (d) Giese, B. Angew. Chem: Int. Ed. Engl. 1985, 24, 553.
5. (e) Hart, D. J. Science 1984, 223, 883.
6. (f) Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1989, 111, 6265, and ref. cited therein,
7. (g) Stork, G.; Reynolds, M. E. Ibid, 1988, 110, 6911.
8. (4) Parker, K. A.; Fokas, D. J. J. Org. Chem., 1994, 59, 3927, 3933.
9. (5) (a) Westwood, S. W. J. Am. Chem. Soc., 1988, 110, 2565.
10. (b) Griller, D.; Schmid, P.; Ingold, K. U. Can. J. Chem., 1979, 57, 831.
11. (6) (a) Tanner, D. D.; Rahimi, P. M. J. Org. Chem., 1979, 44, 1674.
12. (b) Bowman, W. R.; Stephenson, P. T.; Young, A. R. Tetrahedron Lett., 1995, 36, 5623.
13. (c) Sunggak, K.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882.
14. (7) (a) Warkentin, J.; Tomaszweski, M. Tetrahedron Lett. 1992, 33, 2123.
15. (b) Tomaszweski, M.; Warkentin, J. J. C. S. Chem. Commun. 1993, 966.
16. (8) Takano, S.; Suzuki, M.; Ogasawara, K. Heterocycles, 1994, 149.
17. (9) (a) Kraus, G. A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939.
18. (b) Kuivila, H.; Menapace, L. W. J. Am. Chem. Soc. 1964, 86, 3047.
19. (10) (a) Kunka, C. P. A.; Warkentin, J. Can. J. Chem., 1990, 68, 575.
20. (b) Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. J. Am. Chem. Soc., 1968, 90, 4182.
21. (11) Baldwin, J. E. J. C. S Chem. Commun. 1976, 734.
22. (12) Giese, B.; Dupuis, J.; Ruegge, D.; Fischer, H.; Korth, H.-G.; Sustmann, R. Angew. Chem. Int. Ed. Engl. 1984, 23, 896.
23. (13) Yoshida, Y.; Tamaru, Y.; Yamada, Y. Synthesis 1983, 474.
24. (14) (a) Frejd, T.; Klingstedt, T. Synthesis, 1987, 40.
25. (b) Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem., 1978, 43, 1684.
26. (15) Meerwein, H. In Organic Syntheses Collective Volumes; Baumgarten, H., Ed.; John Wiley & Sons: New York, 1988, Vol. 6, p. 1019.
27. (16) Crabb, T.A.; Soilleux, S.L. J. Chem. Soc. Perkin Trans 1 1985, 7, 1381.
28. (17) The reduced starting material 5 was independently synthesized from the commercially available 2-phenethylamine via the same route used for the synthesis of 3. See ref. 19.
29. (18) The following amounts of starting imidate 3 isolated from each run was: run 1: 20%; run 2: 33%; run 3: 0%.
30. (19) Kiessling, A. J. Hydrolytic and Radical Cyclization Chemistries of Imidate Esters, and the Photochemical Rearrangement of 1-Azabicyclo[2.2.2]octenones; Ph.D. Dissertation: University of Delaware, 1996.