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Synlett 1995; 1995(5): 425-426
DOI: 10.1055/s-1995-4984
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One-pot Synthesis of α,γ-Disubstituted Tetronic Acids from α-Hydroxyallyl Esters: A Novel ”Tandem-Wittig-Claisen”-Reaction

Rainer Schobert* , Stephan Müller, Hans-Jürgen Bestmann
  • *Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestraße 42, D-91054 Erlangen, Germany
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Publication Date:
31 December 2000 (online)

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A novel ”one-pot”-method for the synthesis of α,γ-disubstituted tetronic acids 1 from readily accessible allylic esters of α-hydroxy acids 5 and keteneylidene triphenylphosphorane 6 has been developed. The underlying ”Tandem-Wittig-Claisen” reaction proceeds under mild and neutral conditions giving rise to high yields and optional isolation of unrearranged intermediates 9.

Tetronic Acids - Wittig Olefination - Claisen Rearrangement - α-Hydroxyesters - Tandem Reaction