New chiral oxazoline-phosphite ligands for the enantioselective copper- catalyzed 1,4-addition of organozinc reagents to enones

Tetrahedron

Volumn 56, Issue 18, 2000, Pages 2879-2888

  Escher, Iris H ^a   Pfaltz, Andreas ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Addition reactions; Asymmetric induction; Copper and compounds; Oxazolines

Indexed keywords

BIPHENYL DERIVATIVE; COPPER; CYCLOPENTENONE; DIETHYLZINC; KETONE DERIVATIVE; NAPHTHYL GROUP; ORGANOMETALLIC COMPOUND; OXAZOLINE DERIVATIVE; PHOSPHITE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034725069     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00143-5     Document Type: Article

References (36)

1. (a) Perlmutter, P. In Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series, Vol. 9; Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1992.
2. (b) Yamamoto, Y. In Houben-Weyl, 4th ed., E21, Vol. 4; Helmchen, G; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Chapter 1.5.2.1.
3. (c) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin/Heidelberg, 1999; Chapter 31.1.
4. Rossiter B.E., Swingle N.M. Chem. Rev. 92:1992;771.
5. (a) Ahn, K. H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178.
6. (b) Van Klaveren, M.; Lambert, F.; Eijkelkamp, D. J. F. M.; Grove, D. M.; van Koten, G. Tetrahedron Lett. 1994, 35, 6135.
7. (c) Van Koten, G. Pure Appl. Chem. 1994, 66, 1455.
8. (d) Spescha, M.; Rihs, G. Helv. Chim. Acta 1993, 76, 1219.
9. (e) Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275.
10. (f) Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. I 1993, 153.
11. Zhou Q.-L., Pfaltz A. Tetrahedron. 50:1994;4467.
12. (a) Soai, K.; Okudo, M.; Okamoto, M. Tetrahedron Lett. 1991, 32, 95.
13. (b) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205.
14. (c) de Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1467.
15. (d) Corma, A.; Iglesias, M.; Martín, M. V.; Rubio, J.; Sánches, F. Tetrahedron: Asymmetry 1992, 3, 845.
16. Alexakis A., Frutos J.C., Mangeney P. Tetrahedron: Asymmetry. 4:1993;2427.
17. Feringa B.L., Pineschi M., Arnold A., Imbos R., de Vries A.H.M. Angew. Chem. Int. Ed. Engl. 36:1997;2620.
18. Alexakis A., Vastra J., Burton J., Benhaim C., Mangeney P. Tetrahedron Lett. 39:1998;7869.
19. Keller E., Maurer J., Naasz R., Schader T., Meetsma A., Feringa B.L. Tetrahedron: Asymmetry. 9:1998;2409.
20. Prétôt R., Lloyd-Jones G.C., Pfaltz A. Pure Appl. Chem. 70:1998;1035.
21. Knöbel A.K.H., Escher I.H., Pfaltz A. Synlett. 1997;1429.
22. Yan M., Chan A.S.C. Tetrahedron Lett. 40:1999;6645.
23. (a) Cram, D. J. J. Org. Chem. 1980, 49, 391.
24. (b) Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253.
25. (a) Suzuki A. Pure Appl. Chem. 1994, 66, 213 method A.
26. (b) Simonsen, K. B.; Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 7536.
27. Lingenfelter D.S., Helgeson R.C., Cram D.J. J. Org. Chem. 56:1981;625.
28. (a) Morgan, J.; Pinhey, J. T. J. Chem. Soc. Perkin Trans. I 1990, 715.
29. (b) Hawthorne, M. F. J. Org. Chem. 1958, 23, 1576.
30. Toda F., Tanaka K., Iwata S. J. Org. Chem. 54:1989;3007.
31. Toda F., Tanak K. J. Org. Chem. 53:1988;3607.
32. r=26.7 (S)/27.7 min (R).
33. Artz S.P., de Grandpre M.P., Cram D.J. J. Org. Chem. 50:1985;1486.
34. Fuji K., Kawabata T., Kuroda A. J. Org. Chem. 60:1995;1914.
35. r=21.4 (S, R, S) min 32% yield.
36. r=23.9 (R) min, t=29.4 (S) min.