Intramolecular C–H insertion catalyzed by dirhodium(II) complexes using CO2 as ...

• Author(s): Zakrzewska, Malgorzata E. ; Cal, Pedro M.S.D. ; Candeias, Nuno R. ; Bogel-Lukasik, R. ; Afonso, Carlos A.M. ; Ponte, Manuel Nunes ; Gois, Pedro M.P.
• Date: 2012
• Persistent ID: http://hdl.handle.net/10400.9/1918
• Origin: Repositório do LNEG
• Subject(s): Diazoacetamides; C–H insertion; Dirhodium(II); Lactams; scCO2
• Document Type: Article
• Language: English

Description

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.