An Entry to 5-(1-Alkenyl)-3 (2H)-furanones through Cycloaddition of Phosphorus-Functionalized Nitrile Oxide to Acetylene Alcohols. An Effective Synthesis of …
Cycloaddition of α-(diethoxyphosphoryl) acetonitrile oxide to acetylene alcohols is followed by an alkylation, a reductive cleavage of the N–O bond, and an acid-catalyzed cyclization to form 5-(diethoxyphosphorylmethyl)-3 (2H)-furanones in good yields. Subsequent Horner- Emmons olefination using triethylamine and lithium bromide furnishes E-isomers of 5-(1- alkenyl)-3 (2H)-furanones as major products. This method has been applied to a short ...
