The endocyclic restriction test: Oxygen transfer from N-sulfonyl oxaziridines to alkenes

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1415-1417

  Anderson, David R ^a   Woods, Keith W ^a   Beak, Peter ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009603601     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990969w     Document Type: Article

References (17)

1. For a reviews of N-sulfonyl oxaziridines, see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703. Davis, F. A.; Chen, B.-C. Chem Rev. 1992, 92, 919.
2. For a reviews of N-sulfonyl oxaziridines, see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703. Davis, F. A.; Chen, B.-C. Chem Rev. 1992, 92, 919.
3. (a) Davis, F. A.; Wei, J.; Sheppard, A. C.; Gubernick, S. Tetrahedron Lett. 1987, 28, 5115.
4. (b) Davis, F. A.; Billmers, J. M.; Gosinak, D. J.; Towson, J. C.; Bach R. D. J. Org. Chem. 1986, 45, 4240.
5. (c) Knipe, A. C.; McAuley, I. E.; Khandelwal, Y.; Kansal, V. K. Tetrahedron Lett. 1984, 25, 1411.
6. (a) Bach, R. D.; Andres, J. L.; Davis, F. A. J. Org. Chem. 1992, 57, 613.
7. (b) Bach, R. D.; Coddens, B. A.; McDouall, J. J. W.; Schlegel, H. B.; Davis, F. A. J. Org. Chem. 1990, 55, 3325.
8. (c) Bach, R. D.; Wolber, G. J. J. Am. Chem. Soc. 1984, 106, 1410.
9. Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346.
10. Mithani, S.; Drew, D. M.; Rydberg, E. H.; Taylor, N. J.; Mooibroek, S.; Dmitrienko, G. I. J. Am. Chem. Soc. 1997, 119, 1159.
11. Beak, P. Acc. Chem. Res. 1992, 25, 215.
12. The observation that at 0.01 M a trace of epoxide 10 can be detected is best understood in terms of competitive reaction pathways. As 2 decomposes, its relative concentration decreases and the velocity of the epoxidation 9 increases relative to the epoxidation of 2 (or products derived from 2). Alternatively, the reactivity of the alkene of 9 could be slightly different than the reactivity of the alkene of 2 or products that result from the reaction of 2.
13. Our experiments do not distinguish between planar and spiro transition states. Molecular models suggest that either transition state may be available to 2 and 3.
14. Woods, K. W.; Beak, P. J. Am. Chem. Soc. 1991, 113, 6281. Bach, R. D.; Winter, J. D.; McDouall, J. J. W. J. Am. Chem. Soc. 1995, 117, 8586. Yamabe, S.; Kondou, C.; Minato, T. J. Org. Chem. 1996, 61, 616. Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385.
15. Woods, K. W.; Beak, P. J. Am. Chem. Soc. 1991, 113, 6281. Bach, R. D.; Winter, J. D.; McDouall, J. J. W. J. Am. Chem. Soc. 1995, 117, 8586. Yamabe, S.; Kondou, C.; Minato, T. J. Org. Chem. 1996, 61, 616. Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385.
16. Woods, K. W.; Beak, P. J. Am. Chem. Soc. 1991, 113, 6281. Bach, R. D.; Winter, J. D.; McDouall, J. J. W. J. Am. Chem. Soc. 1995, 117, 8586. Yamabe, S.; Kondou, C.; Minato, T. J. Org. Chem. 1996, 61, 616. Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385.
17. Woods, K. W.; Beak, P. J. Am. Chem. Soc. 1991, 113, 6281. Bach, R. D.; Winter, J. D.; McDouall, J. J. W. J. Am. Chem. Soc. 1995, 117, 8586. Yamabe, S.; Kondou, C.; Minato, T. J. Org. Chem. 1996, 61, 616. Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385.