New enantiopure cyclic β-iminophosphine ligands: Applications in Pd-catalyzed asymmetric allylic substitution

Tetrahedron Letters

Volumn 44, Issue 11, 2003, Pages 2413-2415

  Zablocka, Maria ^a   Koprowski, Marek ^a   Donnadieu, Bruno ^b   Majoral, Jean Pierre ^b   Achard, Mathieu ^c   Buono, Gérard ^c  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^c AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTITUTION REACTION; SYNTHESIS; X RAY DIFFRACTION;

EID: 0037430453     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00182-5     Document Type: Article

References (15)

1. Humphries A.C., Pfaltz A. Vögtle F., Stoddart J.F., Shibasaki M. Stimulating Concepts in Chemistry. 2000;89-103 Wiley-VCH, New York.
2. Helmchen G., Pfaltz A. Acc. Chem. Res. 33:2000;336.
3. McCarthy M., Guiry P.J. Tetrahedron. 5:2001;3809.
4. Pfaltz A., Lautens M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. II:1999;834-884 Springer, Berlin.
5. Hayashi T., Hayashi C., Uozumi Y. Tetrahedron: Asymmetry. 6:1995;2503.
6. Saitoh A., Morimoto T., Achiwa K. Tetrahedron: Asymmetry. 8:1997;3567.
7. Saitoh A., Achiwa K., Morimoto T. Tetrahedron: Asymmetry. 9:1998;741.
8. Saitoh A., Misawa M., Morimoto T. Tetrahedron: Asymmetry. 10:1999;1025.
9. Saitoh A., Misawa M., Morimoto M. Synlett. 1999;480.
10. Jang H.Y., Seo H., Han J.W., Chung Y.K. Tetrahedron Lett. 41:2000;5081.
11. Zablocka M., Igau A., Cenac N., Donnadieu B., Dahan F., Majoral J.-P., Pietrusiewicz M.K. J. Am. Chem. Soc. 117:1995;8083.
12. NMR data are identical to that observed for the analogous racemic compound. See: Cadierno V., Zablocka M., Donnadieu B., Igau A., Majoral J.-P., Skowronska A. J. Am. Chem. Soc. 121:1999;11086.
13. R=7.11 min.
14. 2=0.0641 for all data, GOF=0.859, absolute structure parameter x=0.04(15) All hydrogen atoms were located on a difference Fourier map, but introduced in the refinement as fixed contributors by using a riding model and with an isotropic thermal parameter fixed at 20% higher than those of the carbon atoms to which they are connected, excepted concerning the hydrogen atoms H(8) and H(11) which were isotropically refined. All non-hydrogen atoms were anisotropically refined, and in the last cycles of refinement weighting schemes have been used. Drawings of molecules are performed by using the program ORTEP-32 with 50% probability displacement ellipsoids for non-hydrogen atoms. Crystallographic data (excluding structure factors) for the structure in this paper, have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC.195494. 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).
15. Koprowski M., Sebastian R.-M., Maraval V., Zablocka M., Cadierno V., Donnadieu B., Caminade A.-M., Majoral J.-P. Organometallics. 21:2002;4680.