Chiral Mn(III) salen complex-catalyzed enantioselective epoxidation of nonfunctionalized alkenes using urea-H2O2 adduct as oxidant

Journal of Catalysis

Volumn 219, Issue 1, 2003, Pages 1-7

  Kureshy, Rukhsana I ^a   Khan, Noor Ul H ^a   Abdi, Sayed H R ^a   Singh, Surendra ^a   Ahmed, Irshad ^a   Shukla, Ram S ^a   Jasra, Raksh V ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Catalysis; Chiral; Enantioselective; Kinetics; Manganese; Mechanism; Nonfunctionalized alkenes; Urea H2O2

Indexed keywords

ALKENE DERIVATIVE; EPOXIDE; MANGANESE DERIVATIVE; OXIDIZING AGENT; UREA;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CONCENTRATION RESPONSE; ENANTIOSELECTIVITY; EPOXIDATION; KINETICS; REACTION TIME;

EID: 0141453071     PISSN: 00219517     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0021-9517(03)00163-5     Document Type: Article

References (30)

1. Mijs W.J., De Jonge C.R.H.I. Organic Synthesis by Oxidation with Metal Compounds. 1996;Plenum, New York.
2. Reddy C.C., Hamilton G.A., Madyashta K.M. Biological Oxidation System. 1990;Academic Press, San Diego, CA.
3. Jacobsen E.N., Zhang W., Güler M.L. J. Am. Chem. Soc. 113:1991;6703.
4. Jacobsen E.N., Zhang W., Muci A.R., Ecker J.R., Deng L. J. Am. Chem. Soc. 113:1991;7063.
5. Zhang W., Jacobsen E.N. J. Org. Chem. 56:1991;2296.
6. Palucki M., McCormick G.J., Jacobsen E.N. Tetrahedron Lett. 36:1995;5457.
7. Mukaiyama T., Yamada T., Nagata T., Imagawa K. Chem. Lett. 1993;327.
8. Adam W., Jeko J., Levai A., Nemes C., Patonay T., Sebok P. Tetrahedron Lett. 36:1995;3666.
9. Pietikäinen P. Tetrahedron Lett. 40:1999;1001.
10. Rudolph J., Reddy K.L., Chang J.P., Sharpless K.B. J. Am. Chem. Soc. 119:1997;6189.
11. Lane B.S., Burgess K. J. Am. Chem. Soc. 123:2001;2933.
12. Francis M.B., Jacobsen E.N. Angew. Chem. Int. Ed. 38:1999;937.
13. Katsuki T. J. Mol. Catal: Chem. 113:1996;87.
14. Kureshy R.I., Khan N.H., Abdi S.H.R., Patel S.T., Jasra R.V. Tetrahedron Asymmetry. 12:2001;433.
15. Linde C., Akermark B., Norrby P.O., Svensson M. J. Am. Chem. Soc. 121:1999;5083.
16. Collman J.P., Brauman J.I., Meunir B., Hayashi T., Kodadek T., Rayback S.A. J. Am. Chem. Soc. 112:1990;7980.
17. Palucki M., Finney N.S., Pospisil P.J., Güler M.L., Ishida T., Jacobsen E.N. J. Am. Chem. Soc. 120:1998;948.
18. Kureshy R.I., Khan N.H., Abdi S.H.R., Patel S.T., Iyer P.K., Subramanian P.S., Jasra R.V. J. Catal. 209:2002;99.
19. Perrin D.D., Armarego W.L.F., Perrin D.R. Purification of Laboratory Chemicals. 1981;Pergamon, New York.
20. Bergmann R., Gericke R. J. Med. Chem. 33:1990;429.
21. Kureshy R.I., Khan N.H., Abdi S.H.R., Patel S.T., Iyer P.K., Jasra R.V. Tetrahedron Lett. 43:2002;2665.
22. Pietikäinen P. Tetrahedron. 54:1998;4319.
23. Hughes D.L., Smith G.B., Liu J., Dezyeny G.C., Senanayak C.H., Larsen D.R., Verhoeven T.R., Reider P.J. J. Org. Chem. 62:1997;2222.
24. Collman J.P., Brauman J.I., Meunier B., Raybuck S.A., Kodadek T. Proc. Natl. Acad. Sci. USA. 81:1984;3245.
25. Collman J.P., Brauman J.I., Hampton P.D., Tanaka H., Bohle D.S., Hembre R.T. J. Am. Chem. Soc. 112:1990;7980.
26. Collman J.P., Brauman J.I., Meunier B., Hayashi T., Kodadek T., Raybuck S.A. J. Am. Chem. Soc. 107:1985;2000.
27. Fu H., Look G.C., Zhang W., Jacobsen E.N. Angew. Chem. Int. Ed. Engl. 56:1991;6497.
28. Chang S., Galvin J.M., Jacobsen E.N. J. Am. Chem. Soc. 116:1994;6937.
29. Kureshy R.I., Khan N.H., Abdi S.H.R., Bhatt K.N. Tetrahedron Asymmetry. 1:1993;1693.
30. Srinivasan K., Michaud P., Kochi J.K. J. Am. Chem. Soc. 108:1986;2309.