Asymmetric conjugate addition of diethyl zinc to enones with tartrate chiral phosphite ligands

Tetrahedron Asymmetry

Volumn 8, Issue 19, 1997, Pages 3193-3196

  Alexakis, A ^a   Vastra, J ^a   Burton, J ^a   Mangeney, P ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030821778     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00409-6     Document Type: Article

References (20)

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2. (b) Alexakis A. in Organocopper Reagents, a practical approach, Ed. R. J. K. Taylor, Chapt. 8 p. 159-183. Oxford University Press, 1994
3. For non-covalent external chiral ligands see: (a) Kretchmer, R. A. J. Org. Chem., 1972, 37, 2744-2747.
4. (b) Langer, W.; Seebach, D. Helv. Chim. Acta, 1979, 62, 1710-1722.
5. (c) Leyendecker, F.; Laucher, D. New J. Chem., 1985, 9, 13-19.
6. (d) Alexakis, A.; Mutti, S.; Normant, J. F. J. Am. Chem. Soc., 1991, 113, 6332-6334.
7. (e) Kanai, M.; Koga, K.; Tomioka, K. Tetrahedron Lett., 1992, 33, 7193-7196.
8. (f) Alexakis, A.; Frutos, J. C.; Mangeney, P. Tetrahedron: Asymmetry, 1993, 4, 2427-2430.
9. (a) Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc., 1988, 110, 3175-3182.
10. (b) Ahn, K. H.; Klassen, R. B.; Lippard, S. J. Organometallics, 1990, 9, 3178-3181.
11. (c) Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G. Tetrahedron: Asymmetry, 1991, 2, 1097-1100.
12. (d) Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc., 1992, 114, 3400-3410.
13. (e) Kanai, M.; Tomioka, K. Tetrahedron Lett., 1992, 33, 4275-4278.
14. (f) Kanai, M.; Tomioka, K. Tetrahedron Lett., 1995, 36, 4273-4274.
15. (g) Zhou, Q.-L.; Pfaltz, A. Tetrahedron Lett., 1993, 34, 7725-7728.
16. 2f other groups have dealt with the asymmetric conjugate addition of diethylzinc to enones, catalysed by copper salts: (a) de Vries, A. H. M.; Meetsma, A.; Feringa, B. L. Ang. Chem. Int. Ed. Engl. 1996, 35, 2374-2376.
17. (b) de Vries, A. H. M.; Hof, R. P.; Staal, D.; Kellog, R. M.; Feringa, B. L. Tetrahedron: Asymmetry, 1997, 8, 1539-1543.
18. (c) Wendisch, V.; Sewald, N. Tetrahedron: Asymmetry, 1997, 8, 1253-1257.
19. Alexakis, A.; Vastra, J.; Mangeney, P. submitted for publication.
20. 2Zn (1M sol. in hexane, 7 mL, 7 mmol) was added followed by a solution of the enone (5 mmol) in dichloromethane (3 mL). The reaction was followed by GC until completion. Acidic work-up and chromatography gave the pure adduct.