Remarkable O2-Effect in 1,4-Additions of Diethylzinc to 6-Acyloxy-2H-pyran-3(6H)-ones and 6-Alkoxy-2H-pyran-3(6H)-ones

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1593-1595

  Van Der Deen, Hanneke ^a   Kellogg, Richard M ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000681184     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005843+     Document Type: Article

References (20)

1. Knochel, P.; Almene Perea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275.
2. (a) Feringa, B. L.; de Vries A. H. M. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press Inc.: 1995; Vol. 1, p 151.
3. (b) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; Vries, A. H. M. de Angew. Chem., Int. Ed. Engl. 1997, 36, 2620.
4. (c) Soai, K.; Shibata, T. In Organozinc Reagents, a practical approach; Knochel, P., Jones, P., Eds.; Oxford University Press: 1998; pp 245-261
5. (d) Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283.
6. (a) Paulsen, H.; Koebernick, W.; Koebernick, H. Tetrahedron Lett. 1976, 2297.
7. (b) Paulsen, H.; Koebernick, W. Carbohydr. Res. 1977, 56, 53.
8. See, for example: Rousseau, G.; Slougi, N. J. Am. Chem. Soc. 1984, 106, 7283.
9. (a) Yamamoto, K.; Yamamoto, N. Chem. Lett. 1989, 1149.
10. (b) Shi, M; Itoh, N.; Masaki, Y J. Chem. Res., Synop. 1995, 8, 304.
11. (a) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725.
12. (b) Enders, D.; Kramps, L. Liebigs Ann./Recueil 1997, 1101.
13. (c) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959.
14. Ruy, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335.
15. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189.
16. Quenching of the samples also has to take place under oxygen free conditions, to prevent a fast reaction at the moment of quenching.
17. 4. After evaporation of the solvent, the crude product was obtained as an oil, which could be purified by chromatography (silica, hexanes:EtOAc 2:1), to give 203 mg of 2a as a yellow oil (71%).
18. 13C NMR, and mass) data consistent with the assigned structures.
19. (a) Abraham, M. H. J. Chem. Soc. 1960, 4130.
20. (b) Sosnovsky, J.; Brown, J. H. Chem. Rev. 1966, 66, 529.