Design of a highly efficient catalyst for the oxaziridinium-mediated epoxidation of olefins by Oxone®

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 747-751

  Bohé, Luis ^a   Kammoun, Majed ^a  

^a CNRS   (France)

Author keywords

Epoxidation; Iminium; Oxaziridinium

Indexed keywords

2,3,3 TRIMETHYL 7 NITRO 3,4 DIHYDROISOQUINOLINIUM; ALKENE; CHEMICAL AGENT; ISOQUINOLINE DERIVATIVE; OXAZIRIDINE DERIVATIVE; OXAZIRIDINIUM; SODIUM PEROXIDE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; EPOXIDATION;

EID: 0347418222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.040     Document Type: Article

References (39)

1. (a) Picot A., Milliet P., Lusinchi X. Tetrahedron Lett. 17:1976;1573-1576
2. (b) Picot A., Milliet P., Lusinchi X. Tetrahedron Lett. 17:1976;1577-1580
3. (c) Picot A., Milliet P., Lusinchi X. Tetrahedron. 37:1981;4201-4208.
4. (a) Hanquet G., Lusinchi X. Tetrahedron Lett. 34:1993;5299-5302
5. (b) Bohé L., Lusinchi M., Lusinchi X. Tetrahedron. 55:1999;155-166.
6. Hanquet G., Lusinchi X. Tetrahedron. 50:1994;12185-12200.
7. (a) Hanquet G., Lusinchi X., Milliet P. Tetrahedron Lett. 29:1988;3941-3944
8. (b) Hanquet G., Lusinchi X. Tetrahedron. 53:1997;13727-13738.
9. (a) Bohé L., Hanquet G., Lusinchi M., Lusinchi X. Tetrahedron Lett. 34:1993;7271-7274
10. (b) Bohé L., Lusinchi M., Lusinchi X. Tetrahedron. 55:1999;141-155.
11. Hanquet G., Lusinchi X., Milliet P. C.R. Acad. Sci. Paris. 313:1991;625-628.
12. Aggarwal V.K., Wang H.F. J. Chem. Soc., Chem. Commun. 1996;191-192.
13. Page P.C.B., Rassias G.A., Bethell D., Schilling M.B. J. Org. Chem. 63:1998;2774-2777 Page P.C.B., Rassias G.A., Barros D., Bethell D., Schilling M.B. J. Chem. Soc., Perkin Trans. 1. 2000;3325-3334 Page P.C.B., Rassias G.A., Barros D., Ardakani A., Buckley B., Bethell D., Smith T.A.D., Slawin M.A.Z. J. Org. Chem. 66:2001;6926-6931 Page P.C.B., Rassias G.A., Barros D., Ardakani A., Bethell D., Merifield E. Synlett. 2002;580-582.
14. Page P.C.B., Rassias G.A., Bethell D., Schilling M.B. J. Org. Chem. 63:1998;2774-2777 Page P.C.B., Rassias G.A., Barros D., Bethell D., Schilling M.B. J. Chem. Soc., Perkin Trans. 1. 2000;3325-3334 Page P.C.B., Rassias G.A., Barros D., Ardakani A., Buckley B., Bethell D., Smith T.A.D., Slawin M.A.Z. J. Org. Chem. 66:2001;6926-6931 Page P.C.B., Rassias G.A., Barros D., Ardakani A., Bethell D., Merifield E. Synlett. 2002;580-582.
15. Page P.C.B., Rassias G.A., Bethell D., Schilling M.B. J. Org. Chem. 63:1998;2774-2777 Page P.C.B., Rassias G.A., Barros D., Bethell D., Schilling M.B. J. Chem. Soc., Perkin Trans. 1. 2000;3325-3334 Page P.C.B., Rassias G.A., Barros D., Ardakani A., Buckley B., Bethell D., Smith T.A.D., Slawin M.A.Z. J. Org. Chem. 66:2001;6926-6931 Page P.C.B., Rassias G.A., Barros D., Ardakani A., Bethell D., Merifield E. Synlett. 2002;580-582.
16. Page P.C.B., Rassias G.A., Bethell D., Schilling M.B. J. Org. Chem. 63:1998;2774-2777 Page P.C.B., Rassias G.A., Barros D., Bethell D., Schilling M.B. J. Chem. Soc., Perkin Trans. 1. 2000;3325-3334 Page P.C.B., Rassias G.A., Barros D., Ardakani A., Buckley B., Bethell D., Smith T.A.D., Slawin M.A.Z. J. Org. Chem. 66:2001;6926-6931 Page P.C.B., Rassias G.A., Barros D., Ardakani A., Bethell D., Merifield E. Synlett. 2002;580-582.
17. (a) Armstrong A., Ahmed G., Garnett I., Goacolou K. Synlett. 1997;1075-1076
18. (b) Armstrong A., Ahmed G., Garnett I., Goacolou K., Wailes J.S. Tetrahedron. 55:1999;2341-2352.
19. Minakata S., Takemiya A., Nakamura K., Ryu I., Komatsu M. Synlett. 2000;1810-1812.
20. Wong M.-K., Ho L.-M., Zheng Y.-S., Ho C.-Y., Yang D. Org. Lett. 3:2001;2587-2590.
21. Lacour J., Monchaud D., Marsol C. Tetrahedron Lett. 43:2002;8257-8260.
22. Poisson D., Cure G., Solladié G., Hanquet G. Tetrahedron Lett. 42:2001;3745-3748.
23. (a) Hanquet G., Lusinchi X., Milliet P. Tetrahedron Lett. 28:1987;6061-6064
24. (b) Hanquet G., Lusinchi X., Milliet P. Tetrahedron. 49:1993;423-438.
25. Bohé L., Kammoun M. Tetrahedron Lett. 43:2002;803-805.
26. McCoubey A., Mathieson D.W. J. Chem. Soc. 1951;2851-2853.
27. (a) Schmitz E. Chem. Ber. 91:1958;1133-1140
28. (b) Heer J.P., Hartling J.D., Thompson M. Synth. Commun. 32:2002;2555-2564.
29. 4: C, 43.20; H, 3.99; N, 10.08. Found: C, 43.09; H, 3.72; N, 9.92.
30. Ritter J., Kalish J. Org. Synth. 44:1964;44-47.
31. Larsen R.D., Reamer R.A., Corley E.G., Davis P., Grabowski E.J.J., Reider P.J., Shinkai I. J. Org. Chem. 56:1991;6034-6038.
32. Seeger E., Engel W., Teufel H., Machleidt H. Chem. Ber. 103:1970;1674-1691.
33. 2: C, 64.69; H, 5.92; N, 13.72. Found: C, 64.73; H, 6.05; N, 13.51.
34. 4: C, 47.09; H, 4.94; N, 9.15. Found: C, 46.84; H, 4.64; N, 9.11.
35. 3CD) analysis of the crude product, integrating the C9 methyls at δ 1.31 ppm (s, 3H) and δ 1.33 ppm (m, 3H).
36. 3CD) analysis of the crude product, integrating the oxiranic protons at δ 3.18 ppm (m, 2H, anti-epoxide) and δ 3.23 ppm (m, 2H, syn-epoxide).
37. Kuhn T., Tamm C., Reisen A., Zedner M. Tetrahedron Lett. 30:1989;693-696.
38. 3CD) analysis of the crude product, integrating the oxiranic proton (C6-H) signals at δ 3.05 ppm (d, J=1.7 Hz, 1H, β-epoxide) and δ 2.86 ppm (d, J=4.4 Hz, 1H, α-epoxide).
39. Kirk D.N., Hartshorn M.P. Steroid Reaction Mechanisms. 1968;Elsevier, Amsterdam. pp 69-77.