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Synthesis 2000; 2000(8): 1160-1165
DOI: 10.1055/s-2000-6323
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Regioselective Alkylation of Lithium Dienediolates of α,β-Unsaturated Carboxylic Acids

Eva M. Brun* , Salvador Gil, Ramón Mestres, Margarita Parra
  • *Departament de Química Orgánica, Universitat de València, Burjassot, València, Spain
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Publication Date:
31 December 2000 (online)

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Lithium carboxylic acids dienediolates are regioselectively alkylated at the α-carbon by reaction with tosylates derived from both primary and secondary alcohols. Both regio- and diastereoselectivity are improved when compared with those obtained in the corresponding alkylation with alkyl halides.

lithium enolates - alkylation - alkyl sulfonates - carboxylic acids - diastereoselectivity