Chemistry Letters

An Entry to 5-(1-Alkenyl)-3 (2H)-furanones through Cycloaddition of Phosphorus-Functionalized Nitrile Oxide to Acetylene Alcohols. An Effective Synthesis of …

O Tsuge, S Kanemasa, H Suga

Index: Tsuge, Otohiko; Kanemasa, Shuji; Suga, Hiroyuki Chemistry Letters, 1987 , p. 323 - 326

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Citation Number: 14

Abstract

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 ...