Unprecedented loss of stereochemical integrity at a neighboring quaternary carbon during oxidation of a highly substituted cyclohexanol

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1721-1724

  Paquette, Leo A ^a   Branan, Bruce M ^a   Stepanian, Marshall ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; COMPUTER SIMULATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0029922072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00118-9     Document Type: Article

References (17)

1. Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A., Ed. John Wiley and Sons, Chichester, 1995.
2. (a) Negri, J. T.; Rogers, R. D.; Paquette, L. A. J. Am. Chem. Soc. 1991, 113, 5073.
3. (b) Paquette, L. A.; Negri, J. T.; Rogers, R. D. J. Org. Chem. 1992, 57, 3947.
4. (a) Paquette, L. A.; Branan, B. M.; Friedrich, D.; Edmondson, S. D.; Rogers, R. D. J. Am. Chem. Soc. 1994, 116, 506.
5. (b) Branan, B. M.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 7658.
6. (c) Paquette, L. A.; Branan, B. M.; Rogers, R. D. J. Org. Chem. 1995, 60, 1852.
7. Paquette, L. A.; Meehan, G. V.; Marshall, S. J. J. Am. Chem. Soc. 1969, 91, 6779.
8. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
9. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
10. Review: Tidwell, T. T. Org. React. 1990, 39, 297.
11. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 399.
12. Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13.
13. +) calcd 378.2042, obsd 378.2027.
14. +) calcd 378.2042, obsd 378.2030.
15. We thank Prof. Robin Rogers (Northern Illinois University) for the crystallographic determination.
16. Paquette, L. A.; Stepanian, M.; Branan, B. M.; Bauer, C. B.; Rogers, R. D. submitted for publication.
17. We thank the National Science Foundation and Hoechst Marion Roussel for their support of this research.