Artículos de revistas
Chemo-, Regio- And Stereoselective Heck Arylation Of Allylated Malonates: Mechanistic Insights By Esi-ms And Synthetic Application Toward 5-arylmethyl-γ-lactones
Registro en:
Organic Letters. American Chemical Society, v. 16, n. 19, p. 5180 - 5183, 2014.
15237060
10.1021/ol502529v
2-s2.0-84907701915
Autor
Oliveira C.C.
Marques M.V.
Godoi M.N.
Regiani T.
Santos V.G.
Santos E.A.F.D.
Eberlin M.N.
Sa M.M.
Correia C.R.D.
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) 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. 16 19 5180 5183 CNR; São Paulo Research Foundation; 2011/23832-6; FAPESP; São Paulo Research Foundation; 2013/07600-3; FAPESP; São Paulo Research Foundation Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Beletskaya, I.P., Cheprakov, A.V., (2000) Chem. Rev., 100, p. 3009 Dounay, A.B., Overman, L.E., (2003) Chem. 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