Base-induced rearrangements of bicyclo[2.2.1] and bicyclo[2.2.2]alkene-derived epoxides to ketones and alcohols

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 887-888

  Hodgson, David M ^a   Marriott, Robert E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031035694     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02432-X     Document Type: Article

References (10)

1. Crandall, J. K.; Apparu, M. Org. React. (N. Y.) 1983, 29, 345-443; Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
2. Crandall, J. K.; Apparu, M. Org. React. (N. Y.) 1983, 29, 345-443; Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
3. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384.
4. Zefirov, N. S.; Kasyan, L. I.; Gnedenkov, L. Y.; Shashkov, A. S. Cherepanova, E. G. Tetrahedron Lett. 1979, 949-950.
5. Isolated total yields of chromatographically homogeneous spectroscopically pure products are reported.
6. Murray, R. W.; Pillay, M. K.; Jeyaraman, R. J. Org. Chem. 1988, 53, 3007-3011.
7. Chizkov, A. O.; Zefirov, N. S.; Zyk, N. V.; Morrill, T. C. J. Org. Chem. 1987, 52, 5647-5655.
8. 2, 0 °C to 25 °C, 16 h, 76%].
9. Evans, D. A.; Golob, A. M.; Mandel, N. S.; Mandel, G. S. J. Am. Chem. Soc. 1978, 100, 8170-8174.
10. The structure of alcohol 18 was determined by X-ray crystallographic analysis of the corresponding 3,5-dinitrobenzoate. Full details will be reported at a later date.