A simple and versatile method for alkene epoxidation using aqueous hydrogen peroxide and manganese salophen catalysts

Tetrahedron Letters

Volumn 47, Issue 12, 2006, Pages 1923-1926

  Liu, Shih Yuan ^a   Nocera, Daniel G ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMINOSALOL; ALKENE; ALKENE DERIVATIVE; BUFFER; ESTER; HALIDE; HYDROGEN PEROXIDE; KETONE; MANGANESE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYST; EPOXIDATION; PH;

EID: 32644489470     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.074     Document Type: Article

References (52)

1. K. Srinivasan, P. Michaud, and J.K. Kochi J. Am. Chem. Soc. 108 1986 2309 2320
2. W. Zhang, J.L. Loebach, D.R. Wilson, and E.N. Jacobsen J. Am. Chem. Soc. 112 1990 2081 2083
3. R. Irie, K. Noda, Y. Ito, N. Matsumoto, and T. Katsuki Tetrahedron Lett. 31 1990 7345 7348
4. M. Beller Adv. Synth. Catal. 346 2004 107 108
5. E.N. Jacobsen Adv. Synth. Catal. 346 2004 109
6. C. Venturello, E. Alneri, and M. Ricci J. Org. Chem. 48 1983 3831 3833
7. K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, and R. Noyori J. Org. Chem. 61 1996 8310 8311
8. W.A. Herrmann, R.W. Fischer, and D.W. Marz Angew. Chem., Int. Ed. Engl. 30 1991 1638 1641
9. J. Rudolph, K.L. Reddy, J.P. Chiang, and K.B. Sharpless J. Am. Chem. Soc. 119 1997 6189 6190
10. P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artiles, M. Fort, and D. Mansuy J. Am. Chem. Soc. 110 1988 8462 8470
11. A. Thellend, P. Battioni, and D. Mansuy J. Chem. Soc., Chem. Commun. 1994 1035 1036
12. S.L.H. Rebelo, M.M.Q. Simões, M.G.P.M.S. Neves, A.M.S. Silva, and J.A.S. Cavaleiro Chem. Commun. 2004 608 609
13. D. De Vos, and T. Bein Chem. Commun. 1996 917 918
14. C. Bolm, D. Kadereit, and M. Valacchi Synlett 1997 687 688
15. A. Berkessel, and C. Sklorz Tetrahedron Lett. 40 1999 7965 7968
16. M.B. Francis, and E.N. Jacobsen Angew. Chem., Int. Ed. 38 1999 937 941
17. M.C. White, A.G. Doyle, and E.N. Jacobsen J. Am. Chem. Soc. 123 2001 7194 7195
18. M.K. Tse, C. Döbler, S. Bhor, M. Klawonn, W. Mägerlein, H. Hugl, and M. Beller Angew. Chem., Int. Ed. 43 2004 5255 5260
19. K. Matsumoto, Y. Sawada, B. Saito, K. Sakai, and T. Katsuki Angew. Chem., Int. Ed. 44 2005 4935 4939
20. M.K. Tse, M. Klawonn, S. Bhor, G. Döbler Anilkumar, H. Hugl, W. Mägerlein, and M. Beller Org. Lett. 7 2005 987 990
21. R. Noyori, M. Aoki, and K. Sato Chem. Commun. 2003 1977 1986
22. B.S. Lane, and K. Burgess Chem. Rev. 103 2003 2457 2473
23. G. Grigoropoulou, J.H. Clark, and J.A. Elings Green Chem. 5 2003 1 7
24. 4th ed. J.I. Kroschwitz M. Howe-Grant Kirk-Othmer Encyclopedia of Chemical Technology Vol. 13 1995 John Wiley & Sons New York 961
25. 5th ed. B. Elvers S. Hawkins M. Ravenscroft G. Schulz Ullmann's Encyclopedia of Industrial Chemistry Vol. A13 1989 VCH New York 443
26. T. Schwenkreis, and A. Berkessel Tetrahedron Lett. 34 1993 4785 4788
27. R. Irie, N. Hosoya, and T. Katsuki Synlett 1994 255 256
28. P. Pietikäinen Tetrahedron Lett. 35 1994 941 944
29. P. Pietikäinen Tetrahedron 54 1998 4319 4326
30. P. Pietikäinen J. Mol. Catal. A 165 2001 73 79
31. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S.T. Patel, and R.V. Jasra Tetrahedron: Asymmetry 12 2001 433 437
32. A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, G. Baum, and D. Fenske J. Mol. Catal. A 113 1996 321 342
33. C.-Y. Yeh, C.J. Chang, and D.G. Nocera J. Am. Chem. Soc. 123 2001 1513 1514
34. C.J. Chang, C.-Y. Yeh, and D.G. Nocera J. Org. Chem. 67 2002 1403 1406
35. C.J. Chang, L.L. Chng, and D.G. Nocera J. Am. Chem. Soc. 125 2003 1866 1876
36. L.L. Chng, C.J. Chang, and D.G. Nocera Org. Lett. 5 2003 2421 2424
37. C.J. Chang, M.C.Y. Chang, N.H. Damrauer, and D.G. Nocera Biochim. Biophys. Acta 1655 2004 13 28
38. S.-Y. Liu, and D.G. Nocera J. Am. Chem. Soc. 127 2005 5278 5279
39. L. Deng, and E.N. Jacobsen J. Org. Chem. 57 1992 4320 4323
40. S. Chang, N.H. Lee, and E.N. Jacobsen J. Org. Chem. 58 1993 6939 6941
41. B.D. Brandes, and E.N. Jacobsen J. Org. Chem. 59 1994 4378 4380
42. V.K. Sivasubramanian, M. Ganesan, S. Rajagopal, and R. Ramaraj J. Org. Chem. 67 2002 1506 1514
43. E.N. Jacobsen, W. Zhang, and M.L. Güler J. Am. Chem. Soc. 113 1991 6703 6704
44. M. Palucki, N.S. Finney, P.J. Pospisil, M.L. Güler, T. Ishida, and E.N. Jacobsen J. Am. Chem. Soc. 120 1998 948 954
45. B.S. Lane, and K. Burgess J. Am. Chem. Soc. 123 2001 2933 2934
46. B.S. Lane, M. Vogt, V.J. DeRose, and K. Burgess J. Am. Chem. Soc. 124 2002 11946 11954
47. Y. Chen, and J.-L. Reymond Tetrahedron Lett. 36 1995 4015 4018
48. T. Strassner, and K.N. Houk Org. Lett. 1 1999 419 421
49. L. Cavallo, and H. Jacobsen Angew. Chem., Int. Ed. 39 2000 589 592
50. L. Cavallo, and H. Jacobsen Eur. J. Inorg. Chem. 2003 892 902
51. M.P. Feth, C. Bolm, J.P. Hildebrand, M. Köhler, O. Beckmann, M. Bauer, R. Ramamonjisoa, and H. Bertagnolli Chem. Eur. J. 9 2003 1348 1359
52. W. Zhang, and E.N. Jacobsen J. Org. Chem. 56 1991 2296 2298