Conformational biasing in 1,3-oxidative rearrangements of dienols

Heterocycles

Volumn 74, Issue C, 2007, Pages 225-231

  Majetich, George ^a   Nishide, Hisaya ^a   Phillips, Ryan M ^a   Yu, Jianhua ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 40749119382     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-07-s(w)62     Document Type: Article

References (15)

1. Btichi G., and Egger B. J. Org. Chem. 36 (1971) 2021
2. Grieco P.A. J. Org. Chem. 37 (1972) 2363
3. Liu Z.-J., and Rong G.-B. Synth. Commun. 16 (1986) 871
4. Corey E.J., and Suggs J.W. Tetrahedron Lett. (1975) 2647
5. Corey E.J., and Schmidt G. Tetrahedron Lett. (1980) 731
6. Dauben W.G., and Michno D.M. J. Org. Chem. 42 (1977) 682
7. Babler J.H., and Coghlin M.J. Synth. Commun. 6 (1976) 469
8. Paquette L.A., Crouse G.D., and Sharma A.K. J. Am. Chem. Soc. 104 (1982) 4411
9. Majetich G., Condon S.M., Hull K., and Ahmad S. Tetrahedron Lett. 30 (1989) 1033
10. For other oxidative routes for the preparation of [3-vinylic cycloalkeneones, see:. Jin Z., and Fuchs P. J. Am. Chem. Soc. 116 (1994) 599
11. Trost B.M., and Schmidt T. J. Am. Chem. Soc. 110 (1988) 2301-2303
12. All yields are isolated yields. The spectroscopic data obtained for all new compounds were fully consistent with the assigned structures.
13. 2 and stirred at rt for 8 to 14. Standard ethereal workup, followed by chromatography, provided the yields cited.
14. 2O, 4:1) to provide 803 mg (81% yield) of 3-ethenyl-2-cyclohexenone which was homogeneous by TLC.
15. Capon B., and Kwok F.-C. Tetrahedron Lett. 27 (1986) 3275