Prenylation reaction performed with catalytically generated potassium prenal dienolate

Synlett

Volumn , Issue 12, 1998, Pages 1399-1401

  Cahard, Dominique ^a   Duhamel, Lucette ^a   Lecomte, Sandrine ^a   Poirier, Jean Marie ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002788534     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1955     Document Type: Article

References (10)

1. Duhamel, P.; Cahard, D.; Poirier, J.M. J. Chem. Soc. Perkin Trans. 1 1993, 2509-2511.
2. Cahard, D.; Desmurs, J.R.; Duhamel, L.; Duhamel, P.; Poirier, J.M. Fr. Patents 93.079.65 and 93.079.66.
3. Cahard, D.; Poirier, J.M.; Duhamel, P. Tetrahedron Lett, 1998, 39, 7093-7096.
4. Cazeau, P.; Duboudin, F.; Molines, F.; Laporte, O.; Dunoguès, J. Tetrahedron 1987, 43, 2089.
5. In some experiments the O-silylated hydroxy dihydropyran was inferred in the crude reaction mixture, but due to its high propensity to hydrolyse during the work-up it was never obtained in the expected yield.
6. 3c was synthesised by prenylation of benzaldehyde and served as the starting aldehyde for the new prenylation reaction.
7. 2 (302.4): calcd C, 79.42; H, 10.00; found: C, 79.57; H, 10.16.
8. Olson, G.L. Hoffmann La Roche. US Patent 1976 3, 997, 529.
9. Bennani, Y.L.; Boehm, M.F. J. Org. Chem. 1995, 60, 1195-1200.
10. HIBAR Merck Licrosorb Si 60, 5μm column, 5% ethyl acetate-hexane, 1.5 mL/min, 23 °C, λ = 366 nm. The mixture of stereoisomers of retinal can be easily isomerised to the E isomer according to Mukaiyama, T.; Ishida, T. Chem. Lett. 1975, 1201-1203. Also U.S. Patent Eastman Kodak 1961, 3, 013, 080; Patent AEC 1, 288, 972, C07c, Patent AEC 1, 291, 622, C07c.