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Synthesis 1991; 1991(8): 644-646
DOI: 10.1055/s-1991-26534
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Stereoselective Synthesis of Alkyl α-(1,3-Alkadien-2-yl)acetates and -propionates by Allene Claisen Rearrangement

Ulrike Behrens* , Christian Wolff, Dieter Hoppe
  • *Institut für Organische Chemie der Universität Kiel, Olshausenstr. 40-60, D-2300 Kiel, Germany
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Publication Date:
29 April 2002 (online)

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Configurationally homogeneous (4-hydroxy-1,2-alkadienyl) N,N-diisopropylcarbamates react with trialkyl orthocarboxylates to afford the title compounds stereoselectively. Stereochemical assignment of the highly substituted 1,3-alkadienes is accomplished NMR-spectroscopically by means of couplings constants 3 J(13C-1H) or 3 J (29Si-1H).

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