Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-dihydrofurans by Coinage Metal-Catalyzed Cyclo-isomerization of Phosphorylated α-Hydroxyallenes

• Main Authors: Valerij Ch. Christov, Ismail E. Ismailov, Ivaylo K. Ivanov
• Format: Article
• Language: English
• Published: MDPI AG 2015-04-01
• Series: Molecules
• Subjects: phosphorylated α-hydroxyallenes; cycloisomerization; coinage metal catalysts; 2,5-dihydrofurans
• Online Access: http://www.mdpi.com/1420-3049/20/4/7263

Phosphorylated α-hydroxyallenes 1 and 2 were smoothly converted into the corresponding 2,5-dihydrofurans 3 and 4 in an 5-endo-trig cycloisomerization reaction by using 5 mol % of coinage metal salts as catalyst. Experimental conditions such as the type of the solvent, the reaction temperature, the mol % and the type of the catalyst were optimized. This mild and efficient cyclization method can be applied to dimethyl 1-hydroxyalkyl-alka-1,2-dienephosphonates 1 and 2-diphenylphosphinoyl-2,3-dien-1-ols 2a–c and 3-diphenylphosphinoyl-3,4-dien-2-ols 2d,e, furnishing 3-phosphorylated 2,5-dihydrofurans 3 and 4 in very good yields.