Regio- and stereoselective synthesis of aziridino epoxides from cyclic dienes

Journal of Organic Chemistry

Volumn 71, Issue 4, 2006, Pages 1653-1657

  Sureshkumar, Devarajulu ^a   Maity, Susama ^a   Chandrasekaran, Srinivasan ^a,b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; OLEFINS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

AZIRIDINATION; CYCLIC DIENE; CYCLIC DIENE DERIVATIVES;

STEREOCHEMISTRY;

ALKADIENE; AZIRIDINE DERIVATIVE; CARVONE; EPOXIDE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; EPOXIDATION; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 33644536073     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052357x     Document Type: Article

References (27)

1. (a) Viehe, H. G.; Merenyi, R.; Francotte, E. J. Am. Chem. Soc. 1977, 99, 2340-2342.
2. (b) Zipperer, B.; Mueller, K. H.; Gallenkamp, B.; Hildebrand, R.; Fletschinger, M.; Burer, D.; Pillat, M.; Hunkler, D.; Knothhe, L.; Fritz, H.; Prinzbach, H. Chem. Ber. 1998, 121, 757.
3. (c) Francotte, E.; Merenyi, R.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1978, 17, 936-937.
4. (d) Francotte, E.; Merenyi, R.; Coyette, B. V.; Viehe, H. G. Helv. Chim. Acta 1981, 64, 1208-1218.
5. (e) Sana, M.; Leroy, G.; Vaerman, J. L.; Viehe, H. G. Can. J. Chem. 1990, 68, 1625-1628.
6. (f) Vaerman, J. L.; Viehe, H. G. Tetrahedron 1989, 45, 3183-3188.
7. (g) Prinzbach, H.; Mueller, K. H.; Kaiser, C.; Hunkler, D. Tetrahedron Lett. 1980, 21, 3475-3478.
8. (h) Vogel, E.; Klug, H. H.; Schaefer-Ridder, M. Angew. Chem. 1976, 88, 268.
9. (i) O'Brien, P.; Pilgram, C. D. Tetrahedron Lett. 1999, 40, 8427-8430.
10. Barros, M. T.; Mathias, P. M.; Maycock, C. D.; Ventura, M. R. Org. Lett. 2003, 5, 4321-4323.
11. (a) Schilling, S.; Rinner, U.; Chan, C.; Ghiviriga, I.; Hudlicky, T. Can J. Chem. 2001, 79, 1659-1667.
12. (b) Hudlicky, T.; Rinner, U.; Gonzalez, D.; Akgun, H.; Schilling, S.; Siengalewicz, P.; Martinot, T. A.; Pettit, G. R. J. Org. Chem. 2002, 67, 8726-8753.
13. O'Brien, P.; Pilgram, C. D. Org. Biomol. Chem. 2003, 1, 523-534.
14. Sureshkumar, D.; Koutha, S.; Chandrasekaran, S. J. Am. Chem. Soc. 2005, 127, 12760-12761.
15. Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844-6845.
16. (a) Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett. 1975, 4, 361-362.
17. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744-6746.
18. Knight, J. G.; Muldowney, M. P. Synlett 1995, 949-951.
19. (a) Last, L. A.; Fretz, E. R.; Coates, R. M. J. Org. Chem. 1982, 47, 3211-3219.
20. (b) Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 467;
21. Org. Synth. 1972, 49, 62.
22. O'Brien, P.; Childs, A. C.; Ensor, G. J.; Hill, C. L.; Kirby, J. P.; Dearden, M. J.; Oxenford, S. J.; Rosser, C. Org Lett. 2003, 5, 4955-4957.
23. (a) Mehta, G.; Ramesh, S. S.; Bera, M. K. Chem. Eur. J. 2003, 9, 2264-2272.
24. (b) Kamata, K.; Nakagawa, Y.; Yamaguchi, K.; Mizuno, N. J. Catal. 2004, 224, 224-228.
25. (c) Thummel, R. P.; Rickborn, B. J. Org. Chem. 1972, 37, 4250-4254.
26. cis-Bromonium ion I is 2.35 kcal/mol more stable than the corresponding trans-bromonium ion (see the Supporting Information).
27. Klein, E.; Ohloff, G. Tetrahedron 1963, 19, 1091-1099.