Subscribe to RSS
2-Fluoro-2-buten-4-olide, a New Fluorinated Synthon. Preparation; 1,2-, 1,4- and Tandem Additions
31 December 2000 (online)
2-Fluoro-2-buten-4-olide (1) was prepared either by transformation of D-erythronolactone or by Wittig-Horner reaction of ethyl (diethoxyphosphoryl)fluoroacetate with acetoxyacetaldehyde followed by ring closure. It can be transformed by 1,2-addition of nitrogen or hard carbon nucleophiles to fluorinated hydroxyamides or diols and by 1,4-addition of soft carbon nucleophiles to β-alkylated 2-fluorobutan-4-olides. Tandem addition leads to α,β disubstituted 2-fluorobutan-4-olides which are intermediates for the synthesis of fluorinated lignans.
2-fluoro-2-buten-4-olide - 1,2-addition - 1,4-addition - tandem addition