An investigation into oxo analogues of molybdenum olefin metathesis complexes as epoxidation catalysts for alkenes

Tetrahedron Letters

Volumn 50, Issue 38, 2009, Pages 5344-5346

  Anderson, James C ^a   Smith, Neil M ^b   Robertson, Michelle ^c   Scott, Mark S ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLYL ALCOHOL; MOLYBDENUM;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; EPOXIDATION;

EID: 68049098122     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.011     Document Type: Article

References (33)

1. Ko S.Y., Lee A.W.M., Masamune S., Reed III L.A., Sharpless K.B., and Walker F.J. Science 220 (1983) 949
2. Nicolaou K.C., Winssinger N., Pastor J., Ninkovic S., Sarabria F., He Y., Vourloumis D., Yang Z., Li T., Giannakakou P., and Hamel E. Nature 387 (1997) 268
3. Gagnon S.D. In: Mark H.F., Bikales N.M., Overberger C.G., Menges G., and Kroschwitz J.I. (Eds). Encyclopedia of Polymer Science and Engineering Vol. 6 (1985), John Wiley & Sons, New York 273-307
4. Darensbourg D.J., Mackiewicz R.M., Phelps A.L., and Billodeaux D.R. Acc. Chem. Res. 37 (2004) 836
5. Jørgensen K.A. Chem. Rev. 89 (1989) 431
6. Jørgensen K.A., and Schiøtt B. Chem. Rev. 90 (1990) 1483
7. Katsuki T. Adv. Synth. Catal. 344 (2002) 131
8. de Vos D.E., Sels B.F., and Jacobs P.A. Adv. Synth. Catal. 345 (2003) 457
9. Brill W.F., and Indictor N. J. Org. Chem. 30 (1965) 2074
10. For reviews, see:. Thiel W.R. In: Meyer G., Naumann D., and Wesemann L. (Eds). Inorganic Chemistry Highlights (2002), Wiley-VCH, Weinheim 123
11. Deubel D.V., Frenking G., Gisdakis P., Herrmann W.A., Rösch N., and Sundermeyer J. Acc. Chem. Res. 37 (2004) 645
12. For a selection of achiral molybdenum epoxidation catalysts, see:. Kühn F.E., Zhao J., Abrantes M., Sun W., Afonso C.A.M., Branco L.C., Gonçalves I.S., Pillinger M., and Romão C.C. Tetrahedron Lett. 46 (2005) 47
13. Bruno S.M., Balua S.S., Valente A.A., Almeida Paz F.A., Pillinger M., Sousa C., Klinowski J., Freire C., Ribeiro-Claro P., and Gonçalves I.S. J. Mol. Catal. A: Chem. 270 (2007) 185
14. Brito J.A., Teruel H., Muller G., Massou S., and Gómez M. Inorg. Chim. Acta 361 (2008) 2740
15. Jimtaisong A., and Luck R.L. Inorg. Chem. 45 (2006) 10391
16. Petrovski Z., Valente A.A., Pillinger M., Dias A.S., Rodrigues S.S., Romão C.C., and Gonçalves I.S. J. Mol. Catal. A: Chem. 249 (2006) 166
17. Freund C., Abrantes M., and Kühn F.E. J. Organomet. Chem. 691 (2006) 3718
18. Kühn F.E., Groarke M., Bencze E., Herdtweck E., Prazeres A., Santos A.M., Calhorda M.J., Romão C.C., Gonçalves I.S., Lopes A.D., and Pillinger M. Chem. Eur. J. 8 (2002) 2370
19. Bruno S.M., Pereira C.C.L., Balula M.S., Nolasco M., Valente A.A., Hazell A., Pillinger M., Ribeiro-Claro P., and Gonçalves I.S. J. Mol. Catal. A: Chem. 261 (2007) 79
20. Petrovski Z., Pillinger M., Valente A.A., Gonçalves I.S., Hazell A., and Romão C.C. J. Mol. Catal. A: Chem. 227 (2005) 67
21. For examples of chiral molybdenum epoxidation catalysts, see:. Abrantes M., Sakthievel A., Romão C.C., and Kühn F.E. J. Organomet. Chem. 691 (2006) 3137
22. Jain K.R., Herrmann W.A., and Kühn F.E. Coord. Chem. Rev. 252 (2008) 556
23. Barlan A.U., Basak A., and Yamamoto H. Angew. Chem., Int. Ed. 45 (2006) 5849
24. Burke A.J. Coord. Chem. Rev. 252 (2008) 170
25. Zhao J., Herdtweck E., and Kühn F.E. J. Organomet. Chem. 691 (2006) 2199
26. Rammauth R., Al-Juaid S., Motevalli M., Parkin B.C., and Sullivan A.C. Inorg. Chem. 43 (2004) 4072
27. Cross W.B., Anderson J.C., Wilson C., and Blake A.J. Inorg. Chem. 45 (2006) 4556
28. Sharpless K.B., and Verhoeven T.R. Aldrichim. Acta 12 (1979) 63
29. Hill J.G., Rossiter B.E., and Sharpless K.B. J. Org. Chem. 48 (1983) 3607
30. 4 was originally used by Sharpless due to information suggesting that it minimised by-product formation. See Ref. 9a.
31. tBuOOH (12.1 mmol of a 5.5 M solution in decane, 3.0 equiv). The reaction mixture was heated to 90 °C and monitored by TLC or HPLC until the starting material had been consumed, which was less than 4 h for all the examples studied. The reaction mixture was cooled to rt and the solvent removed under vacuum to obtain a residue. Purification by silica gel column chromatography gave pure epoxides that possessed identical physical and spectroscopic properties to those reported.
32. Hanna T.A., Ghosh A.K., Ibarra C., Mendez-Rojas M.A., Rheingold A.L., and Watson W.H. Inorg. Chem. 43 (2004) 1511
33. iPr analogue of 3 could not be isolated. Complex 2b gave an identical yield of cis-stilbene oxide as 2a.