Enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones using chiral oxazoline-phosphite ligands

Synlett

Volumn , Issue 12, 1997, Pages 1429-1431

  Knöbel, Andreas K H ^a   Escher, Iris H ^a   Pfaltz, Andreas ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000813657     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1048     Document Type: Article

References (31)

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., E21b, Vol. 4; Helmchen, G; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. (Eds.); Thieme: Stuttgart, 1995; chapter 1.5.2.1.
3. Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
4. Feringa, B. L.; de Vries, A. H. M. in Advances in Catalytic Processes, Vol. 1; Doyle, M. P. (Ed.); JAI Press: Greenwich, Connecticut, 1995; p. 151.
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. 1 1993, 153.
11. a) Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467.
12. b) Knöbel, A. K. H.; Lloyd-Jones, G. C.; Pfaltz, A.; unpublished work.
13. a) Soai, K.; Okudo, M.; Okamoto, M. Tetrahedron Lett. 1991, 32, 95.
14. b) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205.
15. c) De Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1467.
16. d) Corma, A.; Iglesias, M.; Martin, M. V.; Rubio, J.; Sánches, F. Tetrahedron: Asymmetry 1992, 3, 845.
17. a) De Vries, A. H. M.; Meetsma, A.; Feringa, B. L. Angew. Chem. 1996, 108, 2526;
18. Angew. Chem. Int. Ed. 1996, 35, 2374.
19. b) For the use of related phosphorus ligands, see: Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427 and earlier papers.
20. Feringa, B. L.; lecture at the 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS), Göttingen, July 24, 1997.
21. a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
22. b) Pfaltz, A. Acta Chem. Scand. 1996, 50, 189.
23. a) Prétôt, R.; Pfaltz, A. Angew. Chem., in press.
24. b) Prétôt, R.; Dissertation, University of Basel, 1997.
25. Micropore filter, 0.45 μm (Schleicher & Schuell, Spartan 13/20).
26. r = 45.5, 45.8 min (major enantiomer), estimated error ±5% (not completely baseline-separated).
27. Posner, G. H.; Frye, L. L. Isr. J. Chem. 1984, 24, 88.
28. Brienne, M.-J.; Ouannes, C; Jacques, J. Bull. Soc. Chim. France 1967, 613.
29. D according to Corey, E. J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114.
30. The (R)-configuration was assigned by comparison with commercial (R)-(+)-methylcyclohexanone (Aldrich).
31. For a review of functionalized zinc reagents, see: Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.