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Switch of Selectivity in the Synthesis of α-Methylene-γ-Lactones: Palladium-Catalyzed Intermolecular Carboesterification of Alkenes with Alkynes


  • This work was supported by the National Natural Science Foundation of China (21172076 and 20932002), the National Basic Research Program of China (973 Program) (2011CB808600), a doctoral fund from the Ministry of Education of China (20090172110014), the Guangdong Natural Science Foundation (10351064101000000), and the Fundamental Research Funds for the Central Universities (2010ZP0003).


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Three in one: A highly efficient and mild PdII-catalyzed carboesterification of alkenes with carboxylic alkyne derivatives proceeds through a domino-type alkyne–alkene coupling/C[BOND]O-bond formation (see scheme). The stereoselectivity is controlled by the choice of substrates and temperature. The reaction provides a convenient method for the construction of naturally occurring biologically active compounds with α-methylene-γ-lactone skeletons.