Enantioselective conjugate addition of diethylzinc to enones with chiral copper-QUIPHOS catalyst influence of the addition of water on the enantioselectivity

European Journal of Organic Chemistry

Volumn , Issue 13, 2000, Pages 2507-2511

  Delapierre, Guillaume ^a   Constantieux, Thierry ^a   Brunel, Jean Michel ^a   Buono, Gérard ^a  

^a Ecole Centrale Marseille   (France)

Author keywords

1,4 Addition; Asymmetric synthesis; Copper; Diethylzinc; Enones; N Ligands; P ligands; QUIPHOS

Indexed keywords

COPPER; DIETHYLZINC; LIGAND; WATER;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033925206     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:13<2507::AID-EJOC2507>3.0.CO;2-T     Document Type: Article

References (39)

1. [1f] A. Alexakis, C. Benhaïm, X. Fournioux, A. van den Heuvel, J. M. Levêque, S. March, S. Rosset, Synlett 1999, 1811-1813.
2. [1f] A. Alexakis, C. Benhaïm, X. Fournioux, A. van den Heuvel, J. M. Levêque, S. March, S. Rosset, Synlett 1999, 1811-1813.
3. [1f] A. Alexakis, C. Benhaïm, X. Fournioux, A. van den Heuvel, J. M. Levêque, S. March, S. Rosset, Synlett 1999, 1811-1813.
4. [1f] A. Alexakis, C. Benhaïm, X. Fournioux, A. van den Heuvel, J. M. Levêque, S. March, S. Rosset, Synlett 1999, 1811-1813.
5. [1f] A. Alexakis, C. Benhaïm, X. Fournioux, A. van den Heuvel, J. M. Levêque, S. March, S. Rosset, Synlett 1999, 1811-1813.
6. [1f] A. Alexakis, C. Benhaïm, X. Fournioux, A. van den Heuvel, J. M. Levêque, S. March, S. Rosset, Synlett 1999, 1811-1813.
7. B. L. Feringa, A. H. M. de Vries, in: Advances in Catalytic Processes (ed.: M. P. Doyle), JAI Press Inc., Greenwich, ConNecticut, 1995, Vol. 1, 151-192.
8. [3a] A. Alexakis, S. Mutti, J. F. Normant, J. Am. Chem. Soc. 1991, 113, 6332-6334.
9. [3b] Q. L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467-4478. -
10. [3c] M. Kanai, K. Koga, K. Tomioka, Tetrahedron Lett. 1992, 33, 7193-7196. -
11. [3d] M. Kanai, K. Koga, K. Tomioka, J. Chem. Soc., Chem. Commun. 1993, 1248-1249. -
12. [3e] Y. Nakagawa, M. Kanai, Y. Nagaoka, K. Tomioka, Tetrahedron 1998, 54, 10295-10307.
13. [3f] M. Kanai, Y. Nakagawa, K. Tomioka, Tetrahedron 1999, 55, 3831-3842.
14. [4a] A. Alexakis, J. Vastra, P. Mangeney, Tetrahedron Lett. 1997, 38, 7745-7748.
15. [4b] A. Alexakis, J. Burton, J. Vastra, P. Mangeney, Tetrahedron Asymmetry 1997, 8, 3987-3990.
16. [4c] A. Alexakis, J. Vastra, J. Burton, P. Mangeney, Tetrahedron Lett 1998, 39, 7869-7872.
17. [4d] M. Kanai, K. Tomioka, Tetrahedron Lett. 1995, 24, 4275-7278.
18. [5a] O. Pamies, G. Net, A. Ruiz, C. Claver, Tetrahedron Asymmetry 1999, 10, 2007-2014.
19. [5b] M. Yan, A. S. C. Chan, Tetrahedron Lett. 1999, 40, 6645-6648.
20. [5c] M. Yan, L. W. Yang, K. Y. Wong, A. S. C. Chan, Chem. Commun. 1999, 11-12.
21. [6a] B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. de Vries, Angew. Chem. Int. Ed. Engl. 1997, 36, 2620-2623.
22. [6b] R. Naasz, L. A. Arnold, M. Pineschi, E. Keller, B. L. Feringa, J. Am. Chem. Soc. 1999, 121, 1104-1105. -
23. [6c] R. Imbos, M. H. G. Brilman, M. Pineschi, B. L. Feringa, Org. Lett. 1999, 1, 623-625. -
24. [6d] J. P. G. Versleijen, A. M. van Leusen, B. L. Feringa, Tetrahedron Lett. 1999, 40, 5803-5806.
25. [6e] A. H. M. de Vries, A. Meetsna, B. L. Feringa, Angew. Chem. Int. Ed. Engl. 1996, 35, 2374-2376.
26. A. K. H. Knöbel, I. H. Escher, A. Pfaltz, Synlett 1999, 1429-1431.
27. J. M. Brunel, T. Constantieux, G. Buono, J. Org. Chem. 1999, 64, 8940-8942.
28. [9a] J. M. Brunel, T. Constantieux, A. Labande, F. Lubatti, G. Buono, Tetrahendron Lett. 1997, 38, 5971-5974. -
29. [9b] T. ConStantieux, J. M. Brunel, A. Labande, G. Buono, Synlett 1998, 49-50. -
30. [9c] G. Muchow, J. M. Brunel, M. Maffe, O. Pardigon, G. Buono, Tetrahedron 1998, 54, 10435-10448.
31. J. M. Brunel, B. Del Campo, G. Buono, Tetrahedron Lett. 1998, 39, 9663-9666.
32. A. Alexakis, J. C. Frutos, P. Mangeney, Tetrahedron Asymmetry 1993, 4, 2431-2434.
33. Such an observation has been already mentioned by Feringa et al.: E. Keller, J. Maurer, R. Naasz, T. Schader, A. Meetsma, B. L. Feringa, Tetrahedron Asymmetry 1998, 9, 2409-2413. Moreover, the exact nature of the species generated is still undetermined, and the presence of mixed (EtZn)O(ZnX) aggregates seems to be the most plausible hypothesis. See for example: G. Parkin, Inorganic Synthesis: Zinc: Organometallic Chemistry 1992, 4451-4467 and references cited therein.
34. Such an observation has been already mentioned by Feringa et al.: E. Keller, J. Maurer, R. Naasz, T. Schader, A. Meetsma, B. L. Feringa, Tetrahedron Asymmetry 1998, 9, 2409-2413. Moreover, the exact nature of the species generated is still undetermined, and the presence of mixed (EtZn)O(ZnX) aggregates seems to be the most plausible hypothesis. See for example: G. Parkin, Inorganic Synthesis: Zinc: Organometallic Chemistry 1992, 4451-4467 and references cited therein.
35. Q. L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467.
36. [14b] C. Girard, H. B. Kagan, Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
37. [14b] C. Girard, H. B. Kagan, Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
38. 2Zn to the copper complex, followed by π-complexation of the resulting copper alkylzinc ion to the enone carbonyl (see ref.[6]).
39. 3. The space group was determined to be P2vc from the systematic absences. A total of 9651 reflections were collected at T = 298 K. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 142335. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) +44(1223)336-033, E-mail: deposit@ccdc.cam.ac.uk].