title: N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles.
abstract: We report catalytic, intramolecular hydroacylations of N-allylimidazole-2-carboxaldehydes and N-allylbenzimidazole-2-carboxaldehydes. These exo-selective hydroacylations occur in the presence of a N-heterocyclic carbene catalyst to generate 5,6-dihydro-7H-pyrrolo[1,2-α]imidazol-7-ones and 1,2-dihydro-3H-benzo[d]pyrrolo[1,2-α]imidazol-2-ones in high yields (66-99%). In addition, hydroacylations of N-allylimidazole-2-carboxaldehydes in the presence of a chiral, non-racemic NHC catalyst occur, forming 5,6-dihydro-7H-pyrrolo[1,2-α]imidazol-7-ones in moderate-to-high yields (39-98%) with modest enantioselectivities (56-79% ee).
authors.affiliation: Department of Chemistry, Iowa State University, Ames, IA 50011, USA. lstanley@iastate.edu.
authors.forename: James A
authors.initials: JA
authors.lastname: Walker
authors.affiliation: Department of Chemistry, Iowa State University, Ames, IA 50011, USA. lstanley@iastate.edu.
authors.forename: Levi M
authors.identifier: http://orcid.org/0000-0001-8804-1146
authors.initials: LM
authors.lastname: Stanley