Synthesis and reactions of exo-camphorylsulfonyloxaziridine

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3625-3630

  Davis, Franklin A ^a   Reddy, Rajarathnam E ^b   Kasu, Parimala V N ^a   Portonovo, Padma S ^a   Carroll, Patrick J ^c  

^a TEMPLE UNIVERSITY   (United States)

^b DREXEL UNIVERSITY   (United States)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR DERIVATIVE; OXAZIRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030914483     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961991v     Document Type: Article

References (19)

1. Davis, F. A.; Thimma Reddy, R.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428.
2. Davis, F. A.; Thimma Reddy, R. J. Org. Chem. 1992, 57, 2599.
3. (a) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919.
4. (b) Davis, F. A.; Chen, B.-C. (in Stereoselective Synthesis. Helmchen, G., Hoffman, R. W., Mulzer, J., Schaumann, E., Eds.) Houben-Weyl 1995, E21e, 4497.
5. For reviews on the oxygen transfer reactions of oxaziridines, see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703. Davis, F. A.; Thimma Reddy, R. Comp. Heterocycl. Chem. II. In press.
6. For reviews on the oxygen transfer reactions of oxaziridines, see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703. Davis, F. A.; Thimma Reddy, R. Comp. Heterocycl. Chem. II. In press.
7. Bach, R. D., Wolber, G. J. Am. Chem. Soc. 1984, 106, 1410.
8. Bach, R. D.; Coddens, B. A.; McDouall, J. J. W.; Schlegel, H. B.; Davis, F. A. J. Org. Chem. 1990, 55, 3325.
9. Davis, F. A.; Billmers, J. M.; Gosciniak, D. J.; Towson, J. C.; Bach, R. D. J. Org. Chem. 1986, 51, 4240.
10. Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, S. M. J. Am. Chem. Soc. 1990, 112, 6679.
11. Davis, F. A.; Weismiller, M. C.; Murphy, C. K.; Thimma Reddy, R.; Chen, B.-C. J. Org. Chem. 1992, 57, 7274.
12. Morris, J.; Wishka, D. G. J. Org. Chem. 1991, 56, 3549.
13. Hutchinson, J. H.; Money, T. Can. J. Chem. 1984, 62, 1899.
14. Towson, J. C.; Weismiller, M. C.; Lal, G. S.; Sheppard, A. C.; Davis, F. A. Org. Synth. 1990, 69, 158.
15. Goodridge, R. J.; Hambley, T. W.; Haynes, R. K.; Ridley, D. D. J. Org. Chem. 1988, 53, 2881.
16. For a discussion of formation of endo and exo (fenchonesulfonyl)-oxaziridines, see: Wagner, G.; Verfurth, U. Herrmann, R. Z. Naturforsch. 1995, 50b, 283.
17. Kipping, F. A.; Pope, W. J. J. Chem. Soc. 1893, 63, 548.
18. Davis, F. A.; Thimma Reddy, R.; McCauley, J. P., Jr.; Przeslawski, R. M.; Karakal, M. E.; Carroll, P. J. J. Org. Chem. 1991, 56, 809.
19. Bortolini, O.; Campestrini, S.; Di Furia, F.; Modena, G. J. Org. Chem. 1987, 52, 5093.