Diastereoselective and regioselective epoxidations of allylic alcohols by the in situ-generated dioxirane of 2,2,2-trifluoroacetophenone

Tetrahedron

Volumn 56, Issue 7, 2000, Pages 989-992

  Grocock, Estella L ^a   Marples, Brian A ^a   Toon, Richard C ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

Diastereoselection; Dioxiranes; Epoxidation; Regioselection

Indexed keywords

ACETIC ACID DERIVATIVE; ACETOPHENONE DERIVATIVE; ALCOHOL DERIVATIVE; CYCLOHEXENE DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; GERANIOL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034635491     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01081-9     Document Type: Article

References (20)

1. Adam W., Smerz A.K. Bull. Soc. Chim. Belg. 105:1996;581-599.
2. Adam W., Prechtl F., Richter M.J., Smerz A.K. Tetrahedron Lett. 34:1993;8427-8430.
3. Adam W., Smerz A.K. Tetrahedron. 51:1995;13039-13044.
4. Murray R.W., Singh M., Williams B.L., Moncrieff H.M. J. Org. Chem. 61:1996;1830-1841.
5. Adam W., Smerz A.K. J. Org. Chem. 61:1996;3506-3510.
6. Adam W., Mitchell C.M., Paredes R., Smerz A.K., Veloza L.A. Liebigs Ann./Rec. 1997;1365-1369.
7. Wang Z.-X., Shi Y. J. Org. Chem. 63:1998;3099-3104.
8. Yang D., Jiao G.-S., Yip Y.-C., Wong M.-K. J. Org. Chem. 64:1999;1635-1639.
9. Kurihara M., Ito S., Tsutsumi N., Miyata N. Tetrahedron Lett. 35:1994;1577-1580.
10. Boehlow T.R., Buxton P.C., Grocock E.L., Marples B.A., Waddington V.L. Tetrahedron Lett. 39:1998;1839-1842.
11. Harburn J.J., Loftus G.C., Marples B.A. Tetrahedron. 54:1998;11907-11924.
12. Van Horn J.D., Burrow C.J. Tetrahedron Lett. 40:1999;2069-2070. and references cited therein.
13. Dodd D.S., Oehlschlager A.C., Georgopapadakou N.H., Polak A.-M., Hartman P.G. J. Org. Chem. 57:1992;7226-7234.
14. Ohtake H., Higuchi T., Hirobe M. Tetrahedron Lett. 33:1992;2521-2524.
15. Astudillo L., Galindo A., Gonzalez A.G., Mansilla H. Heterocycles. 36:1993;1075-1080.
16. Atkinson R.S., Kelly B.J. J. Chem. Soc., Perkin Trans. 1. 1989;1515-1519.
17. Morimoto T., Hirano M., Koyama T. J. Chem. Soc., Perkin Trans 2. 1985;1109-1116.
18. Amri H., El Gaied M.H. J. Fluorine Chem. 46:1990;75-82.
19. Corser D.A., Marples B.A., Dart R.K. Synlett. 1992;987-989. (cis-epoxide only).
20. Curini M., Epifano F., Marcotullio M.C., Rosati O. Synlett. 1999;777-779.