Alkene epoxidation with urea-hydrogen peroxide complex and PS-DVB supported phthalic anhydride

Tetrahedron Letters

Volumn 46, Issue 10, 2005, Pages 1643-1645

  Ghiron, Chiara ^a   Nannetti, Lorenzo ^b   Taddei, Maurizio ^b  

^a Sienabiotech srl   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

Epoxidation; Peroxyacid; Supported reagents

Indexed keywords

ALKENE; ALKENE DERIVATIVE; HYDROGEN PEROXIDE; METAL; PHTHALIC ANHYDRIDE; RESIN; TRIMELLITIC ANHYDRIDE; UREA;

ARTICLE; EPOXIDATION; ESTERIFICATION; REACTION ANALYSIS;

EID: 13744253136     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.074     Document Type: Article

References (30)

1. P. Hodge Curr. Opin. Chem. Biol. 7 2003 362
2. N.E. Leadbeater, and M. Marco Chem. Rev. 102 2002 3217
3. D.L. Flynn, S.C. Berk, and G.M. Makara Curr. Opin. Drug Discovery Dev. 5 2002 580
4. S.V. Ley, and I.R. Baxendale Nat. Rev. Drug Discovery 1 2002 573
5. A. Kirschning, H. Monenschein, and R. Wittemberg Angew. Chem., Int. Ed. 40 2001 650
6. S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longbottom, M. Nesi, J.S. Scott, R.I. Storer, and S.J. Taylor J. Chem. Soc., Perkin Trans. 1 2000
7. For a soluble polymer-supported Sharpless epoxidation see: H. Guo, X. Shi, S. Qiao, S. Hou, and M. Wang Chem. Commun. 2002 118
8. For the Julia-Colonna chiral epoxidation using polymeric aminocid linked on a TentaGel resin see: A. Berkessel, N. Gasch, K. Glaubitz, and C. Koch Org. Lett. 3 2001 3839
9. R. Saladino, V. Neri, A.R. Pelliccia, and E. Mincione Tetrahedron 59 2003 7403
10. W.-H. Cheung, W.-Y. Yu, W.-P. Yip, N.-Y. Zhu, and C.-M. Che J. Org. Chem. 67 2002 7716 and references cited therein
11. S. Gil, R. Gonzales, R. Mestres, V. Sanz, and A. Zapater React. Funct. Polym. 42 1999 65
12. Methyl ketone attached to polystyrene: A. Shiney, P.K. Rajan, and K. Sreekumar Polym. Int. 41 1996 377
13. ®: T.R. Boehlow, P.C. Buxton, E.L. Grocock, B.A. Marples, and V.L. Waddington Tetrahedron Lett. 39 1998 1839
14. Trifluoromethyl ketone immobilized on silica: E.S. Choong, J.S. Lim, S.C. Kim, K.-J. Lee, and D.Y. Chi Chem. Commun. 2000 2415
15. For a catalytic dihydroxylation of olefins with hydrogen peroxide catalyzed by Nafion NR50 see: Y. Usui, K. Sato, and M. Tanaka Angew. Chem., Int. Ed. 42 2003 5623
16. J.T.W. Kan, and P.H. Toy Tetrahedron Lett. 45 2004 6357
17. S. Masala, and M. Taddei Org. Lett. 1 1999 1355
18. A. Falchi, and M. Taddei Org. Lett. 2 2000 3429
19. L. De Luca, G. Giacomelli, G. Porcu, and M. Taddei Org. Lett. 3 2001 855
20. D. Donati, C. Morelli, A. Porcheddu, and M. Taddei J. Org. Chem. 69 2004 9316
21. P. Brougham, M.S. Cooper, D.A. Cummerson, H. Heaney, and N. Thompson Synthesis 1987 1015
22. H. Böhome Org. Synth. Coll. 3 1955 619
23. See also: F. Fringuelli, R. Germani, F. Pizzo, F. Santinelli, and G. Savelli J. Org. Chem. 57 1992 1198
24. V.A. Yaylayan, M. Siu, J.M. Belanger, and J. Pare Tetrahedron. Lett. 43 2002 9023
25. F. Gaggini, A. Porcheddu, G. Reginato, M. Rodriquez, and M. Taddei J. Comb. Chem. 6 2004 805 Using the quantitative test with dimethoxytrytyl chloride, a loading of about 0.6-0.8 mmol/g was determined
26. M.E. Attardi, and M. Taddei Tetrahedron Lett. 42 2001 2927
27. L.S. Silbert, E. Siegel, and D. Swern J. Org. Chem. 27 1962 1336
28. H. Heaney S.D. Burke R.L. Danheiser Oxidizing and Reducing Agents Handbook of Reagents for Organic Synthesis 1999 J. Wiley & Sons Chichester p 178
29. See also: M.S. Cooper, H. Heaney, A.J. Newbold, and W.R. Sanderson Synlett 1990 533
30. 1H NMR analysis