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Synlett 1997; 1997(8): 986-988
DOI: 10.1055/s-1997-929
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2-Fluoro-2-buten-4-olide, a New Fluorinated Synthon. Preparation; 1,2-, 1,4- and Tandem Additions

Jaroslav Kvíčala1 , Jakub Plocar2 , RůŽena Vlasáková2 , Oldřich Paleta2 , Andrew Pelter3
  • 1Department of Organic Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czeck Republic, Fax 420 2 24354288; e-mail kvicalai@vscht.cz
  • 2Department of Organic Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czeck Republic
  • 3Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea SA2 8PP, United Kingdom
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Publication History

Publication Date:
31 December 2000 (online)

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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