Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc

Journal of Organic Chemistry

Volumn 69, Issue 17, 2004, Pages 5660-5667

  Alexakis, Alexandre ^a   Polet, Damien ^a   Rosset, Stéphane ^a   March, Sébastien ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; OLEFINS; PHENOLS; SUBSTITUTION REACTIONS; ZINC;

CONJUGATE ADDITIONS; ENANTIOSELECTIVITY;

COPPER;

ALKENE DERIVATIVE; AMINE; COPPER; DIETHYLZINC; LIGAND; PHENOL DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 4043151290     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049359m     Document Type: Article

References (28)

1. (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
2. (b) Alexakis, A. In Transition Metal Catalysed Reactions; Murahashi, S.-I., Davies, S. G., Eds.; IUPAC Blackwell Science: Oxford, U.K., 1999; p 303.
3. (c) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 2000; p 1105.
4. (d) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
5. (e) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
6. For a recent review, see: Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236.
7. (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353.
8. (b) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879-2888.
9. (c) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521.
10. (d) Yan, M.; Zhou, Z.-Y.; Chan, A. S. C. Chem. Commun. 2000, 115-116.
11. (c) Borner, C.; Dennis, M. R.; Sinn, E.; Woodward, S. Eur. J. Org. Chem. 2001, 2435-2446.
12. (d) Rimkus, A.; Sewald, N. Synthesis 2004, 135-146.
13. (e) Hua, Z.; Vassar, V. C.; Choi, H.; Ojima, I. Proc. Natl. Acad. Sci. 2004, 101, 5411-5416.
14. Watanabe, T.; Knoepfel, T. F.; Carreira, E. M. Org. Lett. 2003, 5, 4557-4558.
15. Alexakis, A.; Rosset, S.; Allamand, J.; March, S.; Guillen, F.; Benhaim, C. Synlett 2001, 9, 1375-1378.
16. Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263.
17. 2-symmetrical secondary amines in the following: Alexakis, A.; Gille, S.; Prian, F.; Rosset, S.; Ditrich, K. Tetrahedron Lett. 2004, 45, 1449-1451.
18. DeJongh, D. C.; Van Fossen, R. Y. J. Org. Chem. 1972, 37, 1129-1135.
19. Gómez-Lor, B.; Echavarren, A. M.; Santos, A. Tetrahedron Lett. 1997, 38, 5347-5350.
20. Unrau, C. M.; Campbell, M. G.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2773-2776.
21. Qiu, W. U.S. Patent No. US 6077979, 2000; p 3.
22. Collman, J. P.; Zhong, M.; Costanzo, S.; Zhang, C. J. Org. Chem. 2001, 66, 8252-8256.
23. Ueki, M.; Matsumoto, Y.; Jodry, J. J.; Mikami, K. Synlett 2001, 1889-1892. The procedure (personal communication) was described with the kind permission of Prof. Mikami.
24. Moneta, W.; Baret, P.; Pierre, J.-L. Bull. Soc. Chim. Fr. 1988, 6, 995-1004.
25. Huddle, P. A.; Perold, G. W. J. Chem. Soc., Perkin Trans, 1 1980, 2617-2625.
26. Ueki, M.; Matsumoto, Y.; Jodry, J. J.; Mikami, K. Synlett 2001, 1889-1892.
27. Heine, H. W.; Ciaccio, J. A.; Carson, K. G.; Taylor, C. M.; Williams, E. A. J. Org. Chem. 1990, 55, 4039-4043.
28. Buisman, G. J. H.; Van der Veen, L. A.; Klootwijk, A.; De Lange, W. G. J.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M.; Vogt, D. Organometallics 1997, 16, 2929-2939.