Synthesis of 3??Fluorofuran??2 (5H)??ones Based on Z/E Photoisomerisation and Cyclisation of 2??Fluoro??4??hydroxybut??2??enoates

K Pomeisl, J Čejka, J Kvíčala…

Index: Pomeisl, Karel; Cejka, Jan; Kvicala, Jaroslav; Paleta, Oldrich European Journal of Organic Chemistry, 2007 , # 35 p. 5917 - 5925

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Citation Number: 5

Abstract

Abstract Mixtures of some (E)-and (Z)-2-fluoroalk-2-enoates prepared from the corresponding 2-hydroxycarbonyl compounds and ethyl 2-(diethoxyphosphoryl)-2- fluoroacetate have been transformed in high conversions into the target 3-fluorofuran-2 (5H)- ones by an efficient Z/E photoisomerisation of noncyclisable Z isomers followed by acid- catalysed cyclisation. In contrast, the acid-catalysed deprotection of ethyl (E)-and (Z)-4-[ ...