Approaches towards catalytic asymmetric epoxidations with methyltrioxorhenium(VII) (MTO): Synthesis and evaluation of chiral non-racemic 2-substituted pyridines

Journal of Molecular Catalysis A: Chemical

Volumn 235, Issue 1-2, 2005, Pages 285-292

  Da Palma Carreiro, Elisabete ^a   Yong En, Guo ^a   Burke, Anthony J ^a  

^a UNIVERSITY OF ÉVORA   (Portugal)

Author keywords

Asymmetric catalysis; Chiral pyridines; Epoxidation; Methyltrioxorhenium(VII)

Indexed keywords

CATALYSIS; COMPLEXATION; HYDROGEN PEROXIDE; OLEFINS; OXIDATION; REACTION KINETICS; RHENIUM COMPOUNDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; CHIRAL PYRIDINES; EPOXIDATION; METHYLTRIOXORHENIUM(VII);

NITROGEN COMPOUNDS;

EID: 20344374746     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2005.03.022     Document Type: Article

References (34)

1. W.A. Herrmann, R.W. Fischer, and D.W. Marz Angew. Chem. Int. Ed. Engl. 30 1991 1638
2. F.E. Kühn, A. Scherbaum, and W.A. Herrmann J. Organomet. Chem. 689 2004 4149
3. J. Rudolph, K.L. Reddy, J.P. Chiang, and K.B. Sharpless J. Am. Chem. Soc. 119 1997 6189
4. W.A. Herrmann, F.E. Kühn, M.R. Mattner, G.R.J. Artus, M.R. Geisberger, and J.D.G. Correia J. Organomet. Chem. 538 1997 203
5. H. Rudler, J.R. Gregorio, B. Denise, J.-M. Brégeault, and A. Deloffre J. Mol. Catal. A Chem. 133 1998 255
6. S.-W. Park, K.-J. Kim, and S.S. Yoon Bull. Korean Chem. Soc. 21 2000 446
7. S.-W. Park, and S.S. Yoon J. Korean Chem. Soc. 44 2000 81
8. M.J. Sabater, M.E. Domine, and A. Corma J. Catal. 210 2002 192
9. J.J. Haider, R.M. Kratzer, W.A. Herrmann, J. Zhao, and F.E. Kühn J. Organomet. Chem. 689 2004 3735
10. C. Moberg, H. Adolfsson, and K. Warnmark Acta Chem. Scand. 50 1996 195 (and references cited therein)
11. A.L. Gavrilova, and B. Bosnich Chem. Rev. 104 2004 349 (and references cited therein)
12. D.L. Christenson, C.J. Tokar, and W.B. Tolman Organometallics 14 1995 2148
13. W.R. Thiel J. Mol. Catal. A Chem. 117 1997 449 (and references cited therein)
14. P. Ferreira, W.-M. Xue, É. Bencze, E. Herdtweck, and F.E. Kühn Inorg. Chem. 40 2001 5834
15. Y.-E. Guo, A.J. Burke, Unpublished results.
16. B.M. Trost, and I.J. Hachiya Am. Chem. Soc. 120 1998 1104
17. C. Moberg, Department of Organic Chemistry, KTH Chemistry, Stockholm, Sweden, Personal communication.
18. E.A. Mash, K.A. Nelson, S. van Deusen, and S.B. Hemperly Org. Synth. 68 1990 92 103
19. N. Arnaud, C. Picard, L. Cazaux, and P. Tisnès Tetrahedron 53 1997 13757
20. A.J. Burke, A.I. Pisco, E.P. Carreiro, Unpublished results.
21. M.T. Barros, A.J. Burke, and C.D. Maycock Tetrahedron Lett. 40 1999 1583
22. T. Dang, and H.B. Kagan J. Am. Chem. Soc. 94 1972 6430
23. U. Berens, and R. Selke Tetrahedron Asymmetry 7 1996 2055
24. D. Haag, J. Runsink, and H.-D. Scharf Organometallics 17 1998 398
25. M.T. Barros, C.D. Maycock, and A.M.F. Phillips Eur. J. Org. Chem. 2004 1820
26. D.L. Jameson, and K.A. Goldsby J. Org. Chem. 55 1990 4992
27. H. Brunner, R.J. Maier, and M. Zabel Synthesis 2001 2484
28. F.E. Kühn, A.M. Santos, P.W. Roesky, E. Herdtweck, W. Scherer, P. Gisdakis, I.V. Yudanov, C. Di Valentin, and N. Rosch Chem. Eur. J. 12 1999 3603
29. E.P. Carreiro, A.J. Burke, M.J.M. Curto, and A.J.R. Teixeira J. Mol. Catal. A Chem. 217 2004 69
30. H. Adolfsson, C. Copéret, J.P. Chiang, and A.K. Yudin J. Org. Chem. 65 2000 8651 (and references cited therein)
31. F.E. Kühn, A.M. Santos, I.S. Gonçalves, C.C. Romão, and A.D. Lopes Appl. Organomet. Chem. 15 2001 43
32. W.A. Herrmann, F.E. Kühn, M.U. Rauch, J.D.G. Correia, and G. Artus Inorg. Chem. 34 1995 2914
33. C.F. Lane, and J.J. Daniels Org. Synth. Col. 6 1988 719
34. O. Cervinka, and O. Kriz Z. Chem. 12 1972 135 (This paper gave only a specific rotation and boiling point for compound 1)