New carbohydrate-based phosphite-oxazoline ligands as highly versatile ligands for palladium-catalyzed allylic substitution reactions

Advanced Synthesis and Catalysis

Volumn 347, Issue 15, 2005, Pages 1943-1947

  Mata, Yvette ^a   Diéguez, Montserrat ^a   Pàmies, Oscar ^a   Claver, Carmen ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Allylic substitution; Amination; Asymmetric catalysis; C C bond formation; Palladium; Phosphite oxazoline ligand

Indexed keywords

EID: 29144447770     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505192     Document Type: Article

References (28)

1. For recent reviews, see: a) B. M. Trost, D. L. van Vranken, Chem. Rev. 1996, 96, 395;
2. b) M. Johannsen, K. A. Jorgensen, Chem. Rev. 1998, 98, 1689;
3. c) A. Pfaltz, M. Lautens, in: Comprehensive Asymmetric Catalysis, (eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer-Verlag: Berlin, 1999, Vol. 2, Chapter 24;
4. d) G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336;
5. e) B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921.
6. A. M. Masdeu-Bultó, M. Diéguez, E. Martin, M. Gómez, Coord. Chem. Rev. 2003, 242, 159.
7. a) M. Diéguez, O. Pàmies, C. Claver, Chem. Rev. 2004, 104, 3189;
8. b) M. Diéguez, O. Pàmies, A. Ruiz, Y. Díaz, S. Castillón, C. Claver, Coord. Chem. Rev. 2004, 248, 2165;
9. c) M. Diéguez, A. Ruiz, C. Claver, Dalton Trans., 2003, 2957.
10. a) B. Gläser, H. Kunz, Synlett 1998, 53;
11. b) K. Yonehara, T. Hashizume, K. Mori, K. Ohe, S. Uemura, Chem. Commun. 1999, 415;
12. c) K. Yonehara, T. Hashizume, K. Mori, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 9374.
13. Bulky biphenyl phosphites are known to provide larger bite angles than phosphinites. The opening of the bite angle is necessary for high chiral recognition in the Pd-catalyzed alkylation reactions: a) B. M. Trost, D. L. van Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327;
14. b)P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H. Reek, P. Dierkes, Chem. Rev. 2000, 100, 2741.
15. The flexibility offered by the biphenyl moiety can be used to fine-tune the chiral pocket formed upon complexation.
16. To date, phosphite ligands have proven to be highly versatile in Pd-catalyzed asymmetric substitution reactions, see, for example: a) M. Diéguez, O. Pàmies, C. Claver, J. Org. Chem. 2005, 70, 3363;
17. b) O. Pàmies, M. Diéguez, C. Claver, J. Am. Chem. Soc. 2005, 127, 3646;
18. c) M. Diéguez, O. Pàmies, C. Claver, Adv. Synth. Catal. in press.
19. Phosphorochloridites are easily prepared in one step from the corresponding bisphenol as described in: G. J. H. Buisman, P. C. J. Kamer, P. W. N. M. van Leeuwen, Tetrahedron: Asymmetry 1993, 4, 1625.
20. [7]
21. For some successful applications, see: a) P. Dierkes, S. Randechul, L. Barloy, A. De Cian, J. Fischer, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. Int. Ed. 1998, 37, 3116 (ees up to 82%);
22. b) B. M. Trost, A. C. Krueger, R. C. Bunt, J. Zambrano, J. Am. Chem. Soc. 1996, 118, 6520 (ees up to 93%);
23. c) B. Wiese, G. Helmchen, Tetrahedron Letters 1998, 39, 5727 (ees up to 85%);
24. [7b] ees up to 98%;
25. [7c] ees up to 85%.
26. For recent successful applications of Pd-catalysts, see: a) S.-L. You, X.-Z. Zhu, Y.-M. Luo, X.-L. Hou, L.-X. Dai, J. Am. Chem. Soc. 2001, 123, 7471;
27. b) R. Prétôt, A. Pfaltz, Angew. Chem. Int. Ed. 1998, 37, 323;
28. c) R. Hilgraf, A. Pfaltz, Synlett 1999, 1814.