Regioselective addition of the prenal potassium dienolate onto α,β- unsaturated aldehydes. A short access to polyenaldehydes

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7093-7096

  Cahard, Dominique ^a   Poirier, Jean Marie ^a   Duhamel, Pierre ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; RETINAL;

ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; METHODOLOGY; PRENYLATION; REACTION TIME; THERMODYNAMICS;

EID: 0032563847     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01544-5     Document Type: Article

References (9)

1. 1. Duhamel, P.; Cahard, D.; Poirier, J.M. J. Chem. Soc. Perkin Trans 1 1993, 2509-2511. Cahard, D.; Desmurs, J.R.; Duhamel, L.; Duhamel, P.; Poirier, J.M. Fr. Pat. n° 93.079.65 and 93.079.66.
2. 1. Duhamel, P.; Cahard, D.; Poirier, J.M. J. Chem. Soc. Perkin Trans 1 1993, 2509-2511. Cahard, D.; Desmurs, J.R.; Duhamel, L.; Duhamel, P.; Poirier, J.M. Fr. Pat. n° 93.079.65 and 93.079.66.
3. 2. Duhamel, L.; Guillemont, J.; Poirier, J.M.; Chabardes, P. Tetrahedron Lett. 1991, 32, 4495-4498 and Tetrahedron Lett. 1991, 32, 4499-4500.
4. 2. Duhamel, L.; Guillemont, J.; Poirier, J.M.; Chabardes, P. Tetrahedron Lett. 1991, 32, 4495-4498 and Tetrahedron Lett. 1991, 32, 4499-4500.
5. 3 to give after usual work-up compounds 3 and/or 4 which were purified by column chromatography on silica gel (light petroleum-diethyl ether 98:2).
6. 4. No α-reaction product detected even in the crude reaction product.
7. 5. Olson, G.L. Hoffmann La Roche US Patent 3,997,529 (Dec. 14, 1976)
8. 6. To a solution of 0.3 mmol of dihydropyran 3 in 1 ml of a mixture of DMF and toluene (ratio 1:4) was added at room temperature a measured quantity (0.5-3 mole%) of anhydrous pyridine hydrochloride. The reaction mixture was placed into a preheated oil bath regulated at 110°C for 5 minutes, cooled and neutralized with 1 ml of saturated sodium hydrogenocarbonate solution. The organic phase was extracted twice with 2 ml of ether. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and solvent was removed. The crude material was chromatographed (silica gel, light petroleum-diethyl ether 98:2) to afford the polyenal 5.
9. 7. 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