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Synlett 1998; 1998(1): 70-72
DOI: 10.1055/s-1998-1565
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γ-Alkylation of Unsaturated Carboxylic Acids. Stereoselective Synthesis of 2Z- and 2E,6E-3-Methyldeca-2,6-dienoic Acids from 3-Methylbut-2-enoic Acid Through Consecutive Ireland Claisen and Cope Rearrangements

S. Gil* , M. A. Lázaro, M. Parra, E. Breitmaier, R. Mestres
  • *Departament de Química Orgànica, Universitat de València, Dr. Moliner 50, Bujassot, 46100 València, Spain
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Publication Date:
31 December 2000 (online)

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γ-Alkylation of 3-methyl-2-butenoic acid is attained by consecutive Ireland Claisen and Cope rearrangements of its allylic alcohol esters. With E- and Z-2-hexen-1-ol, alkylation occurs stereospecifically with inverted transfer of configuration from the alcohol to the acid moiety, to give 2Z,6E- and 2E,6E-3-methyl-2,6-decadienoic acids, respectively.

Ireland-Claisen - Cope - silylketene acetals - 2,6-dienoic acids - γ-alkylation