Tetrahedron letters

Synthese D′ α-hydroxyallenes α-fonctionnalises a partir D′ α-phenylselenoenals

P Lerouge, C Paulmier

Index: Lerouge, Patrice; Paulmier, Claude Tetrahedron Letters, 1984 , vol. 25, # 19 p. 1987 - 1990

Full Text: HTML

Citation Number: 24

Abstract

Résumé Morpholinobenzeneselenenamide (MBSe) react with enals to form α- phenylselenoenals which undergo Wittig and Horner reactions. We synthetise 1-substituted 3-phenylseleno-1, 3 butadienes. Oxidation and subsequent 2, 3-sigmatropic rearrangement lead to α-fonctionnalized α-hydroxyallenes. This compounds give access to 2, 5 dihydrofurans.

Related Articles:

Selenium stabilized anions. Synthetic transformations based on propargyl selenoxides

[Reich,H.J.; Shah,S.K. Journal of the American Chemical Society, 1977 , vol. 99, # 1 p. 263 - 265]

Capto-dative substituent effects: XIII. C4-bridged radical dimerisation with α-phenylselenoacrylic acid derivatives

[Janousek, Z.; Piettre, S.; Gorissen-Hervens, F.; Viehe, H.G. Journal of Organometallic Chemistry, 1983 , vol. 250, # 1 p. 197 - 202]

Allylic and propargylic phenyl selenide oxygenation by cyclohexanone oxygenase:[2, 3]-sigmatraopic rearrangement of the enzyme-generated selenoxide

[Latham, John A.; Branchaud, Bruce P.; Chen, Y.-C. Jack; Walsh, Christopher Journal of the Chemical Society, Chemical Communications, 1986 , # 7 p. 528 - 530]

More Articles...