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Synlett 1992; 1992(2): 161-164
DOI: 10.1055/s-1992-21303
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Palladium-Catalyzed Allylation of Monoalkyl Derivatives of Meldrum's Acid

Emilia Bernocchi* , Sandro Cacchi, Enrico Morera, Giorgio Ortar
  • *Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi "La Sapienza", P. le A. Moro 5, I-00185 Roma, Italy
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Publikationsdatum:
08. März 2002 (online)

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5-Monoalkyl derivatives of Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) react with allylic acetates, trifluoroacetates, and carbonates in the presence of catalytic amounts of tetrakis(triphenylphosphine)palladium to produce the corresponding allylated derivatives. With allylic esters containing both disubstituted and trisubstituted double bonds, the reaction shows a very high regioselectivity for attack at the primary carbon atom. The stereochemical outcome of the reaction is dependent on the substitution pattern of the allylic system and on the nature of the ester group.