Fe-catalyzed Decarbonylative Alkylative Spirocyclization of <i>N</i>-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones

Abstract

For the convenient introduction of simple linear/branched alkyl groups into biologically important azaspirocyclohexadienones, a practical Fe-catalyzed decarbonylative cascade spiro-cyclization of N-aryl cinnamamides with aliphatic aldehydes to provide alkylated 1-azaspiro-cyclohexadienones was developed. Aliphatic aldehydes were oxidative decarbonylated into primary, secondary and tertiary alkyl radicals conveniently and allows for the subsequent cascade construction of dual C(sp3)-C(sp3) and C=O bonds via radical addition, spirocyclization and oxidation sequence.

Keywords

• decarbonylation
• alkylation
• spirocyclization
• aldehyde
• cinnamamide