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

Authors


  • 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).

Abstract

original image

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.

Ancillary