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Intramolecular C–H insertion catalyzed by dirhodium(II) complexes using CO2 as the reaction media

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Resumo:In this work, the intramolecular C–H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C–H insertion was also achieved and the β-lactam 14 was obtained in >97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh2(S-PTTL)4. Finally, the dirhodium(II) complex Rh2(OAc)4 was used in two consecutive cycles in which complete conversion to the lactam was observed.
Autores principais:Zakrzewska, Malgorzata E.
Outros Autores:Cal, Pedro M.S.D.; Candeias, Nuno R.; Lukasik, Rafal M.; Afonso, Carlos A.M.; Ponte, Manuel Nunes; Gois, Pedro M.P.
Assunto:Diazoacetamides C–H insertion Dirhodium(II) Lactams scCO2
Ano:2012
País:Portugal
Tipo de documento:artigo
Tipo de acesso:acesso aberto
Instituição associada:Laboratório Nacional de Energia e Geologia, I.P.
Idioma:inglês
Origem:Repositório do LNEG
Descrição
Resumo:In this work, the intramolecular C–H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C–H insertion was also achieved and the β-lactam 14 was obtained in >97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh2(S-PTTL)4. Finally, the dirhodium(II) complex Rh2(OAc)4 was used in two consecutive cycles in which complete conversion to the lactam was observed.