Asymmetric epoxidation of some arylalkenyl sulfones using a modified Juliá-Colonna procedure

Tetrahedron Letters

Volumn 45, Issue 26, 2004, Pages 5073-5075

  Lopez Pedrosa, Jose Maria ^a   Pitts, Michael R ^a   Roberts, Stanley M ^a   Saminathan, Shanthini ^a   Whittall, John ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; EPOXIDE; SULFONE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; EPOXIDATION; JULIA COLONNA EPOXIDATION REACTION; OXIDATION;

DRYAS IULIA;

EID: 2942587132     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.190     Document Type: Article

References (23)

1. Jarvo E.R., Miller S.J. Tetrahedron. 58:2002;2481-2499
2. Banfi S., Colonna S., Molinari H., Juliá S., Guixer J. Tetrahedron. 49:1984;5207-5211
3. Baars S., Drauz K.-H., Krimmer H.-P., Roberts S.M., Sander J., Skidmore J., Zanardi G. Org. Process Res. Dev. 7:2003;509-517
4. Polyamino acid catalysts are available from Lancaster Synthesis Ltd
5. Allen J.V., Drauz K.-H., Flood R.W., Roberts S.M., Skidmore J. Tetrahedron Lett. 40:1999;5417-5420
6. Allen J.V., Bergeron S., Griffiths M.J., Mukherjee S., Roberts S.M., Williamson N.M., Wu L.E. J. Chem. Soc., Perkin Trans. 1. 1998;3171-3179
7. Geller T.P., Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 1999;1397-1398
8. Flood R.W., Geller T.P., Petty S.A., Roberts S.M., Skidmore J., Volk M. Org. Lett. 3:2001;683-685
9. Tsogoeva S.B., Wöltinger J., Jost C., Reichert D., Kühnle A., Krimmer H.-P., Drauz K. Synlett. 2002;707-710
10. Cappi M.W., Chen W.-P., Flood R.W., Liao J.W., Roberts S.M., Skidmore J., Smith J.A., Williamson N.M. Chem. Commun. 1:1998;1159-1160
11. Chen W.-P., Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 1999;103-105
12. Adger B.M., Barkley J.V., Bergeron S., Cappi M.W., Flowerdew B.E., Jackson M.P., McCague R., Nugent T.C., Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 1997;3501-3507
13. Carde L., Davies H., Geller T.P., Roberts S.M. Tetrahedron Lett. 40:1999;5421-5424
14. Carde L., Davies D.H., Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 2000;2455-2463
15. Geller T., Gerlach A., Krueger C.M., Militzer H.-C. Chimica Oggi 21:2003;6
16. Geller, T.; Gerlach, A.; Krueger, C. M.; Militzer, H.-C. Chimica Oggi 2003, 21, 6; Geller, T.; Krueger, C. M.; Militzer, H.-C., preceding paper.
17. Caroff, E.; Flood, R. W.; Heal, W.; Kelly, D. R.; Roberts, S. M. Chem. Commun., in press
18. Lasterra-Sanchez M.E., Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 1995;1467-1468
19. See also Porter M.J., Roberts S.M., Skidmore J. Bioorg. Med. Chem. 7:1999;2145-2156
20. The tert-butyl ester is epoxidized successfully under the triphasic conditions Kroutil W., Lasterra-Sanchez M.E., Maddrell S.J., Mayon P., Morgan P., Roberts S.M., Thornton S.R., Todd C.J., Tüter M. J. Chem. Soc., Perkin Trans. 1. 1996;2837-2844
21. Bentley P.A., Bickley J.F., Roberts S.M., Steiner A. Tetrahedron Lett. 42:2001;3741-3743
22. 4) and concentrated in vacuo to give the product. Purification by flash chromatography (ethyl acetate:hexane) yielded the epoxide
23. The absolute configurations of the epoxysulfones are tentative, having been assigned on the basis of the equivalent epoxidation reactions on unsaturated ketones