Application of chiral dipyridylmethane ligands in the enantioselective palladium-catalyzed allylic alkylation

Journal of Molecular Catalysis A: Chemical

Volumn 220, Issue 2, 2004, Pages 145-151

  Chelucci, Giorgio ^a   Chessa, Simona ^a   Orrù, Gianmauro ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

Allylic alkylation; Chiral dipyridylmethane; Enantioselectivity; Nitrogen heterocycles; Palladium complex

Indexed keywords

ALKYLATION; CATALYST SELECTIVITY; CHEMICAL ANALYSIS; MOLECULAR DYNAMICS; PALLADIUM COMPOUNDS;

CHIRALS; ENANTIONMERS; LIGANDS; PYRIDINE RINGS;

CATALYST ACTIVITY;

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; BIPYRIDINE DERIVATIVE; LIGAND; MALONIC ACID DERIVATIVE; PALLADIUM COMPLEX; TERPENE;

ALKYLATION; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY;

EID: 3843117633     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.05.033     Document Type: Article

References (39)

1. I. Ojiama (Ed.), Catalytic Asymmetric Synthesis, 2nd ed., Wiley, New York, 2000.
2. M. Nogradi (Ed.), Stereoselective Synthesis, VCH, New York, 1995.
3. R. Noyori (Ed.), Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
4. J. Seyden-Penne (Ed.), Chiral Auxiliary and Ligands in Asymmetric Synthesis, Wiley/Interscience, New York, 1995.
5. Kamer P.C.J., van Leeuwen P.W.N.M., Reek J.N.H. Acc. Chem. Res. 34:2001;895
6. van Haaren R.J., Goubitz K., Fraanje J., van Strijdonck G.P.F., Oevering H., Coussens B., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M. Inorg. Chem. 40:2001;3363
7. Chelucci G., Thummel R.P. Chem. Rev. 102:2002;3129
8. Fletcher N.C. J. Chem. Soc., Perkin Trans. 1:2002;1831
9. A.V. Malkov, D. Pernazza, M. Bell, M. Bella, A. Massa, F. Teply, P. Meghani, P. Kocovsky, J. Org. Chem. 68 (2003) 4727.
10. Chelucci G., Loriga G., Murineddu G., Pinna G.A. Tetrahedron Lett. 43:2002;8599
11. Trost M.B., Crawley M.L. Chem. Rev. 103:2003;2921
12. Graening T., Schmalz H.-G. Angew. Chem. 115:2003;2685
13. Graening T., Schmalz H.-G. Angew. Chem. Int. Ed. 115:2003;2580
14. Johannsen M., Jorgensen K.A. Chem. Rev. 98:1998;1689
15. Trost M.B., Van Vranken D.L. Chem. Rev. 96:1996;395
16. (a) M.B. Trost, C. Lee, in: I. Ojima (Ed.), Catalytic Asymmetric Synthesis, Wiley/VCH, New York, 2000, p. 593
17. Helmchen G. J. Organomet. Chem. 576:1999;203
18. (c) A. Pfaltz, M. Lautens, in: E.N. Jacobsen, A. Phaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, Springer, Heidelberg, 1999, p. 833
19. Fache F., Schulz E., Tammasino M.L., Lemaire M. Chem. Rev. 100:2000;2159
20. Togni T.A., Venanzi L.M. Angew. Chem. Int. Ed. 33:1994;497
21. Helmchen G., Pfaltz A. Acc. Chem. Res. 33:2000;336
22. Johnson J.S., Evans D.A. Acc. Chem. Res. 33:2000;325
23. (a) A.V. Malkov, P. Kocovsky, Curr. Org. Chem. (2003) 1737
24. Fletcher N.C. J. Chem. Soc., Perkin Trans. 1:2002;1831
25. (c) E. Schoffers, Eur. J. Org. Chem. (2003) 1145.
26. Leutenegger U., Umbricht G., Fahrni C., von Matt P., Pfaltz A. Tetrahedron. 48:1992;2143
27. Malkov A.V., Baxandale I.R., Bella M., Langer V., Fawcett J., Russell D.R., Mansfield D.J., Valko M., Kocovsky P. Organometallics. 20:2001;673
28. Chelucci G., Caria V., Saba A. J. Mol. Catal. A. 130:1998;51
29. For related results with homobidentate ligands, see: Refs. [7,16,18]. For other examples with etherobidentate ligands, see: Refs. [13,14].
30. For related results with homobidentate ligands, see: Refs. [7,16,18]. For other examples with etherobidentate ligands, see: Refs. [13,14].
31. Bönnemann H., Bogdanovich B., Brignkmann R., He D., Spliethoff B. Angew. Chem. 95:1983;749
32. Bönnemann H., Bogdanovich B., Brignkmann R., He D., Spliethoff B. Angew. Chem., Int. Ed. Engl. 22:1983;728
33. Chelucci G. Tetrahedron-Asymmetr. 6:1995;811
34. Mihelich E.D., Eickhoff D.J. J. Org. Chem. 48:1983;4135
35. M. Gianini, A. von Zelewsky, Synthesis (1996) 702.
36. Y. Bessière-Chrétien, C. Grison, Bull. Soc. Chim. Fr. (1970) 3103.
37. Chelucci G., Pinna G.A., Saba A. Tetrahedron-Asymmetr. 9:1998;531
38. Chelucci G., Saba A., Sanna G., Soccolini F. Tetrahedron-Asymmetr. 11:2000;3427
39. J. K. Rasmussen, A. Hassner, Synthesis (1973) 682.