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Synlett 2001; 2001(1): 0156-0159
DOI: 10.1055/s-2001-9721
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Regiocontrol in Alkylation of Lithium Dienediolates of Unsaturated Carboxylic Acids

Eva M. Brun* , Salvador Gil, Margarita Parra
  • *Departament de Química Orgánica, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot, Spain; Fax +34(9)63 98 31 52; E-mail: Margarita.Parra@uv.es
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Publication Date:
31 December 2001 (online)

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Alkylation of dienediolates from unsaturated carboxylic acids with benzylic halides often results in mixtures of regioisomers. However it can be controlled by adequate modification of the reaction conditions. Thus, addition of DMI leads mainly to the α-regioisomer, whereas addition of 12-crown-4 allows to obtain the γ-regioisomer as the major product from the same reactants.

alkyl halides - carboxylic acids - chelates - regioselectivity - solvent effects