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Chemo-, Regio- and Stereoselective Heck Arylation of Allylated Malonates: Mechanistic Insights by ESI-MS and Synthetic Application toward 5-Arylmethyl-γ-lactones

2014; American Chemical Society; Volume: 16; Issue: 19 Linguagem: Inglês

10.1021/ol502529v

1523-7060

Caio C. Oliveira, Marcelo Volpatto Marques, Marla N. Godoi, Thaís Regiani, Vanessa G. Santos, Emerson A. F. dos Santos, Marcos N. Eberlin, Marcus M. Sá, Carlos Roque D. Correia,

Chemical synthesis and alkaloids

We describe herein a general method for the controlled Heck arylation of allylated malonates. Both electron-rich and electron-poor aryldiazonium salts were readily employed as the aryl-transfer agents in good yields and in high chemo-, regio-, and stereoselectivity without formation of decarboxylated byproducts. Reaction monitoring via ESI-MS was used to support the formation of chelated Pd species through the catalytic cycle. Additionally, some Heck adducts were successfully used in the total synthesis of pharmacologically active γ-lactones.