Synthesis, coordination properties and application of new N,N-ligands based on bornyl and binaphthylazepine chiral backbones in palladium-catalyzed allylic substitution reactions

European Journal of Inorganic Chemistry

Volumn , Issue 17, 2011, Pages 2738-2745

  Bottari, Giovanni ^a,b   Meduri, Angelo ^a,c   Drommi, Dario ^a   Brancatelli, Giovanna ^a   Faraone, Felice ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^c UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Allylic compounds; Asymmetric catalysis; Enantioselectivity; N ligands; Palladium

Indexed keywords

ALKYLATION; ALLYLATION; CATALYSIS; CATALYSTS; CHELATION; ENANTIOSELECTIVITY; LIGANDS; SUBSTITUTION REACTIONS;

ALLYLIC COMPOUNDS; ALLYLIC SUBSTITUTION; ASYMMETRIC CATALYSIS; COORDINATION PROPERTIES; IMINE-AMINE; N LIGANDS; N-LIGANDS; PALLADIUM CATALYST; PALLADIUM-CATALYZED; SYNTHESISED;

PALLADIUM;

EID: 79958028243     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201100113     Document Type: Article

References (30)

1. I. Ojima (Ed.), in: Catalytic Asymmetric Synthesis, 2nd ed., Wiley-VCH, New York, 2000.
2. G.-Q. Lin, Y.-M. Li, A. S. C. Chan (Eds.), in: Principles and Applications of Asymmetric Synthesis, Wiley-VCH, Weinheim, Germany, 2001.
3. B. M. Trost, D. L. van Vranken, Chem. Rev. 1996, 96, 395-422.
4. B. M. Trost, T. Zhang, J. D. Sieber, Chem. Sci. 2010, 1, 427-440.
5. T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691-1692.
6. D. A. Lange, B. Goldfuss, Beilstein J. Org. Chem. 2007, 3, No. 36.
7. G. Helmchen, A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345, and literature cited therein.
8. For selected examples of the application of P,P-ligands in allylic substitution reactions, see, A. Saitoh, M. Misawa, T. Morimoto, Tetrahedron: Asymmetry 1999, 10, 1025-1028.
9. E. Raluy, M. Diéguez, O. Pàmies, J. Org. Chem. 2007, 72, 2842-2850.
10. J. Wassenaar, S. van Zutphen, G. Mora, P. Le Floch, M. A. Siegler, A. L. Spek, J. N. H. Reek, Organometallics 2009, 28, 2724-2734.
11. F. Fernández, A. Gual, C. Claver, S. Castillõn, G. Muller, M. Gõmez, Eur. J. Inorg. Chem. 2010, 758-766.
12. A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345.
13. H. Kubota, M. Nakajima, K. Koga, Tetrahedron Lett. 1993, 34, 8135-8138.
14. P. G. Andersson, A. Harden, D. Tanner, P.-O. Norrby, Chem. Eur. J. 1995, 1, 12-16.
15. P. Gamez, B. Dunjic, F. Fache, M. Lemaire, Tetrahedron: Asymmetry 1995, 6, 1109-1116.
16. G. Chelucci, G. A. Pinna, A. Saba, Tetrahedron: Asymmetry 1998, 9, 531-534.
17. J.-L. Vasse, R. Stranne, R. Zalubovskis, C. Gayet, C. Moberg, J. Org. Chem. 2003, 68, 3258-3270.
18. D. Drommi, M. Saporita, G. Bruno, F. Faraone, P. Scafato, C. Rosini, Dalton Trans. 2007, 1509-1519.
19. M. Saporita, G. Bottari, G. Bruno, D. Drommi, F. Faraone, J. Mol. Catal. A 2009, 309, 159-165.
20. For catalytic applications of camphor-based ligands, see W. Oppolzer, Pure Appl. Chem. 1990, 62, 1241-1250.
21. M. Knollmüller, M. Ferencic, P. Gärtner, K. Mereiter, C. R. Noe, Tetrahedron: Asymmetry 1998, 9, 4009-4020.
22. A. Caselli, G. B. Giovenzana, G. Palmisano, M. Sistic, T. Pilati, Tetrahedron: Asymmetry 2003, 14, 1451-1454.
23. A. Gayet, C. Bolea, P. G. Andersson, Org. Biomol. Chem. 2004, 2, 1887-1893.
24. G. Chelucci, Chem. Soc. Rev. 2006, 35, 1230-1243.
25. G. Blay, L. R. Domingo, V. Hernández-Olmos, J. R. Pedro, Chem. Eur. J. 2008, 14, 4725-4730.
26. T. Mecca, S. Superchi, E. Giorgio, C. Rosini, Tetrahedron: Asymmetry 2001, 12, 1225-1233.
27. J.-P. Mazaleyratt, D. J. Cram, J. Am. Chem. Soc. 1981, 103, 4585-4586.
28. C. Rosini, R. Tanturli, P. Pertici, P. Salvadori, Tetrahedron: Asymmetry 1996, 7, 2971-2982.
29. M. Widhalm, U. Nettekoven, H. Kalchhauser, K. Mereiter, M. J. Calhorda, V. Félix, Organometallics 2002, 21, 315-325.
30. M. Diéguez, O. Pamies, Acc. Chem. Res. 2010, 43, 312-322.