Enantioselective palladium catalyzed allylic amination using new chiral pyridine-phosphine ligands

Synlett

Volumn , Issue 1, 1998, Pages 49-50

  Constantieux, Thierry ^a   Brunel, Jean Michel ^a   Labande, Agnès ^a   Buono, Gérard ^a  

^a Ecole Centrale Marseille   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 25144437546     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1561     Document Type: Article

References (35)

1. (a) Brunner, H. in Topics in Stereochemistry ; Eliel, E.; Wilen, S. H. (Ed.) ; John Wiley & Sons, Inc.; New York, 1988, Vol. 18, pp. 129.
2. (b) Noyori, R.; Kitamura, M. in Modern Synthetic Methods ; Scheffold, R. (Ed.) ; Springer-Verlag, Berlin, Heidelberg, 1989, pp. 115.
3. (c) Ojima, I. (Ed.) in Catalytic Asymmetric Synthesis ; VCH Publishers, Inc.; New York, 1993.
4. (d) Seyden-Penne, J. in Chiral Auxiliaries and Ligands in Asymmetric Synthesis ; John Wiley & Sons, Inc.; New York, 1995.
5. (e) Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
6. Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
7. (a) Trost, B. M.; van Vraken, D. L. Chem. Rev. 1996, 96, 395.
8. (b) Williams, J. M. J. Synlett 1996, 705.
9. (c) Pfaltz, A. Acc. Chem. Res. 1993, 26, 329.
10. (d) Hayashi, T. in Catalytic Asymmetric Synthesis ; Ojima, I. (Ed.) ; VCH Publishers, Inc.; New York, 1993 pp. 325.
11. (e) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
12. (a) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans I 1994, 2065.
13. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
14. (c) Chelucci, G.; Cabras, M. A. Tetrahedron Asymmetry 1996, 7, 965.
15. (d) Von Matt, P.; Pfaltz, A. Angew. Chem. Int. Ed. 1993, 32, 566.
16. (a) Zhou, Q. L.; Pfaltz, A. Tetrahedron 1994, 50, 4467.
17. (b) Newman, L. M.; Williams, J. M.; McCague, R.; Potter, G. A. Tetrahedron Asymmetry 1996, 7, 1597.
18. (c) Langer, T.; Janssen, J.; Helmchem, G. Tetrahedron Asymmetry 1996, 7, 1599.
19. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783.
20. (e) Lambert, F.; Knotter, D. M.; Janssen, M. D.; Van Klaveren, M.; Boersma, J.; Van Koten, G. Tetrahedron Asymmetry 1991, 2, 1097.
21. Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Tetrahedron Lett. 1997, 38, 5971.
22. Various groups have already reported high ee in asymmetric palladium catalyzed allylic amination, for example see : (a) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301.
23. (b) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444.
24. (c) Togni, A.; Burkhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
25. (d) Von Matt, P.; Loiseleur, O.; Koch, G.; Pfaltz, A.; Lebefer, C.; Feucht, T.; Helmchen, G. Tetrahedron Asymmetry 1994, 5, 573.
26. 31P NMR spectroscopy and after 2 h, the solvent was removed under vacuum. The product was purified by column chromatography (eluent : AcOEt/petroleum ether) affording the corresponding ligands 1-4 in good chemical yields and in a total anti diastereoselectivity. Syn diastereomer could not be obtained due to the highly unstable intermediate compound which totally epimerizes at the phosphorus atom to produce the thermodynamic diastereomer anti. (a) Cros, P.; Buono, G.; Peiffer, G.; Denis, D.; Mortreux, A.; Petit, F. New. J. Chem. 1987, 11, 573.
27. (b) Arzoumanian, H.; Buono, G.; Choukrad, M'B.; Petrignani, J. F. Organometallics 1988, 7, 59.
28. (c) Brunel, J. M.; Chiodi, O.; Faure, B.; Fotiadu, F.; Buono, G. J. Organomet. Chem. 1997, 529, 285. The definitions of the syn and anti isomers are according to the position of the pyrrolidine ring and the aryl group. If they are at the same side of the five membered phosphorus-containing ring, we call it a syn isomer; otherwise, it is an anti isomer.
29. 3) 122.1.
30. Akermark, B.; Hansson, S.; Krakenberger, B.; Vitagliano, A.; Zetterberg, K. Organometallics 1984, 3, 679.
31. (b) Akermark, B.; Krakenberger, B.; Hansson, S.; Vitagliano, A. Organometallics 1987, 6, 620.
32. (c) Peña-cabrera, E.; Norrby, P.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299.
33. (a) Blöchl, P. E.; Togni, A. Organometallics 1996, 15, 4125.
34. (b) Burckhardt, U.; Baumann, M.; Togni, A. Tetrahedron Asymmetry 1997, 8, 155.
35. In the structure of diastereomeric complexes 8 and 9, the absolute configuration at the phosphorus atom has been well established by X-ray analysis structure of Iigand 1. Brunel, J. M.; Constantieux, T.; Buono, G. Unpublished results.