Synthesis and evaluation of N,S-compounds as chiral ligands for transfer hydrogenation of acetophenone

Organic and Biomolecular Chemistry

Volumn 1, Issue 2, 2003, Pages 358-366

  Ekegren, Jenny K ^a   Roth, Peter ^a   Källström, Klas ^a   Tarnai, Tibor ^a,b   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b BIOVITRUM AB   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; MOLECULAR STRUCTURE; OXIDATION; REDUCTION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ACETOPHENONE; BICYCLIC SULFOXIDE LIGANDS; CHIRAL LIGANDS;

ORGANIC COMPOUNDS;

GADUS MORHUA;

EID: 0041817833     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208907f     Document Type: Article

References (33)

1. J. C. Bayón, C. Claver and A. M. Masdeu-Bultó, Coord. Chem. Rev., 1999, 73, 193-195.
2. A. M. W. Cargill Thompson, D. A. Bardwell, J. C. Jeffery, L. H. Rees and M. D. Ward, J. Chem. Soc., Dalton Trans., 1997, 721.
3. B. Koning, A. Meetsma and R. M. Kellogg, J. Org. Chem., 1998, 63, 5533.
4. D. Sellmann, P. Bail, F. Knoch and M. Moll, Chem. Ber., 1995, 128, 653.
5. A. Berkessel, J. W. Bats, M. Bolte, T. Neumann and L. Seidel, Chem. Ber. Recl., 1997, 130, 891.
6. W. S. Sheldrick and R. Exner, J. Organomet. Chem., 1990, 386, 375.
7. For recent examples see references 3 and 7. G. Chelucci, N. Culeddu, A. Saba and R. Valenti, Tetrahedron: Asymmetry, 1999, 10, 3537.
8. M. L. Tommasino, M. Casalta, J. A. J. Breuzard and M. Lemaire, Tetrahedron: Asymmetry, 2000, 11, 4835.
9. For examples see references 9-11. J. C. Anderson, R. Cubbon, M. Harding and D. S. James, Tetrahedron: Asymmetry, 1998, 9, 3461 and references cited therein.
10. D. A. Fulton and C. L. Gibson, Tetrahedron Lett., 1997, 38, 2019.
11. M. Kossenjans, M. Soeberdt, S. Wallbaum, K. Harms, J. Martens and H. G. Aurich, J. Chem. Soc. Perkin Trans. 1, 1999, 2353.
12. A. H. M. de Vries, R. P. Hof, D. Staal, R. M. Kellogg and B. L. Feringa, Tetrahedron: Asymmetry, 1997, 8, 1539.
13. M. Touchard, P. Gamez, F. Fache and M. Lemaire, Tetrahedron Lett, 1997, 38, 2275.
14. F. Touchard, F. Fache and M. Lemaire, Tetrahedron: Asymmetry, 1997, 8, 3319.
15. F. Touchard, M. Bernard and M. Lemaire, J. Mol. Cat. A: Chem., 1999, 1.
16. M. Bernard, F. Delbecq, F. Fache, P. Sautet and M. Lemaire, Eur. J. Org. Chem., 2001, 8, 1589.
17. D. G. I. Petra, P. C. J. Kamer, A. L. Spek, H. E. Schoemaker and P. W. N. M. van Leeuwen, J. Org. Chem., 2000, 65, 3010.
18. A. Hage, D. G. I. Petra, J. A. Field, D. Schipper, J. B. P. A. Wijnberg, P. C. J. Kamer, J. N. H. Reek, P. W. N. M. van Leeuwen, R. Wever and H. E. Schoemaker, Tetrahedron: Asymmetry, 2001, 12, 1025.
19. For reviews see references 19 and 20. R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97.
20. M. J. Palmer and M. Wills, Tetrahedron: Asymmetry, 1999, 10, 2045.
21. D. A. Alonso, D. Guijarro, P. Pinho, O. Temme and P. G. Andersson, J. Org. Chem., 1998, 63, 2749.
22. D. A. Alonso, P. Brandt, S. J. M. Nordin and P. G. Andersson, J. Am. Chem. Soc., 1999, 121, 9580.
23. D. A. Alonso, S. J. M. Nordin, P. Roth, T. Tarnai, P. G. Andersson, M. Thommen and U. Pittelkow, J. Org. Chem., 2000, 65, 3116.
24. S. J. M. Nordin, P. Roth, T. Tarnai, D. A. Alonso, P. Brandt and P. G. Andersson, Chem. Eur. J., 2001, 7, 1431.
25. J. K. Ekegren, S. A. Modin, D. A. Alonso and P. G. Andersson, Tetrahedron: Asymmetry, 2002, 13, 447.
26. P. Roth and T. Tarnai, unpublished results.
27. F. Fringuelli, O. Piermatti, F. Pizzo and L. Vaccaro, J. Org. Chem., 1999, 64, 6094.
28. J. Christoffers, Y. Schulze and J. Pickardt, Tetrahedron, 2001, 57, 1765.
29. Z. da Zhang and R. Scheffold, Helv. Chim. Acta, 1993, 76, 2602.
30. C. Anaya de Parrodi, G. E. Moreno, L. Quintero and E. Juaristi, Tetrahedron: Asymmetry, 1998, 9, 2093.
31. M. Chandrasekhar, G. Sekar and V. K. Singh, Tetrahedron Lett., 2000, 41, 10079.
32. M. E. Piotti and H. Alper, J. Am. Chem. Soc., 1996, 118, 111.
33. 2SO resolved this peak into two.