New enantiopure C2 symmetric bis(2-oxazolinyl)cage (Cage-Box) ligands from 4,5-dicyanopyridazine

Tetrahedron Asymmetry

Volumn 16, Issue 24, 2005, Pages 3998-4003

  Cecchi, Marco ^a   Faggi, Cristina ^a   Giomi, Donatella ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKADIENE; ALKENE DERIVATIVE; LIGAND; OXAZOLINE DERIVATIVE; PYRIDAZINE DERIVATIVE; ZINC CHLORIDE;

ARTICLE; CATALYSIS; PRIORITY JOURNAL;

EID: 28944441806     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.10.024     Document Type: Article

References (26)

1. H. Brunner, U. Obermann, and P. Wimmer J. Organomet. Chem. 316 1986 C1 C3
2. H. Brunner, U. Obermann, and P. Wimmer Organometallics 8 1989 821 826
3. For a recent review on oxazoline-based ligands, see: H.A. McManus, and P.J. Guiry Chem. Rev. 104 2004 4151 4202
4. J.K. Whitesell Chem. Rev. 89 1989 1581 1590
5. A. Pfaltz Acc. Chem. Res. 26 1993 339 345
6. For recent reviews on bis(oxazoline) ligands, see: A.K. Ghosh, P. Mathivanan, and J. Cappiello Tetrahedron: Asymmetry 9 1998 1 45
7. K.A. Jørgensen, M. Johannsen, S. Yao, H. Audrain, and J. Thorhauge Acc. Chem. Res. 32 1999 605 613
8. J.S. Johnson, and D.A. Evans Acc. Chem. Res. 33 2000 325 335
9. D. Rechavi, and M. Lemaire Chem. Rev. 102 2002 3467 3493
10. G. Desimoni, G. Faita, and P. Quadrelli Chem. Rev. 103 2003 3119 3154
11. Ref. 2, 4182-4191.
12. T.G. Gant, and A.I. Meyers Tetrahedron 50 1994 2297 2360
13. C. Bolm, K. Weickhardt, M. Zehnder, and T. Ranff Chem. Ber. 124 1991 1173 1180
14. R. Nesi, D. Giomi, S. Turchi, and P. Paoli Tetrahedron 50 1994 9189 9194
15. D. Giomi, R. Nesi, S. Turchi, and R. Coppini J. Org. Chem. 61 1996 6028 6030
16. D. Giomi, R. Nesi, S. Turchi, and E. Mura J. Org. Chem. 65 2000 360 364
17. TLC analyses of the reaction mixture after 24 h already showed the presence of compounds 5a and 6a, as well as the cage starting material.
18. Careful chromatography demonstrated the formation of side products and in particular a small amount (ca. 4-5%) of a species probably coming from 6c by aromatization of one of the two oxazoline rings was detected.
19. For a similar behaviour of oxazoline derivatives, see: H.A. McManus, S.M. Barry, P.G. Andersson, and P.J. Guiry Tetrahedron 60 2004 3405 3416
20. M. Gómez, G. Muller, and M. Rocamora Coord. Chem. Rev. 193-195 1999 769 835
21. P. Braunstein, and F. Naud Angew. Chem., Int. Ed. 40 2001 680 699
22. Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 278139. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
23. N. Walker, and D. Stuart Acta Crystallogr., Sect. A 39 1983 158 166
24. Sheldrick, G. M. sadabs version 2.03, a Program for Empirical Absorption Correction. University of Göttingen, Germany, 1997-2001.
25. A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori, and R. Spagna J. Appl. Crystallogr. 32 1999 115 119
26. Sheldrick, G. M. shelxl97, Program for Crystal Structure Refinement. University of Göttingen, Germany.