Remarkably complex and unpredictable cyclization and rearrangement reactions of cations derived from unsaturated oxiranes

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 8921-8924

  Corey, E J ^a   Roberts, Bryan E ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; EPOXIDE; ETHYLENE OXIDE;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030816979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10426-9     Document Type: Article

References (13)

1. See Sutherland, J. K. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p. 341.
2. (a) Corey, E. J.; Lee, J. J. Am. Chem. Soc. 1993, 115, 8873.
3. (b) Corey, E. J.; Lee, J.; Liu, D. R. Tetrahedron Lett. 1994, 35, 9149.
4. (c) Corey, E. J.; Lin, S. J. Am. Chem. Soc. 1996, 118, 8765.
5. Corey, E. J.; Roberts, B. E. Tetrahedron Lett, preceding papers in this issue.
6. We are indebted to Dr. Mark C. Noe and Dr. Marcus Semones for carrying out the X-ray crystallographic analyses. Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
7. The (S)-(-)-α-methylbenzylammonium group has been omitted from the X-ray structure of 4 for clarity.
8. See however: Corey, E. J.; Wood, H. B., Jr. J. Am. Chem. Soc. 1996, 118, 1982.
9. The 3,5-dinitrobenzoyl group has been omitted from the X-ray structure of 6 for clarity.
10. (a) Corey, E. J.; Daley, D. C. manuscript in preparation.
11. 13C NMR spectra of 2 with the NMR spectra of both the trans and cis isomers of 2 prepared by a different route, namely stereospecific m-CPBA epoxidation of the corresponding olefins.
12. 2Cl distance).
13. This research was supported by the National Science Foundation and the National Institutes of Health.