Jump to main content
Jump to site search

Issue 42, 2016
Previous Article Next Article

N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles

Author affiliations

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).

Graphical abstract: N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 05 Sep 2016, accepted on 28 Sep 2016 and first published on 28 Sep 2016


Article type: Communication
DOI: 10.1039/C6OB01956K
Citation: Org. Biomol. Chem., 2016,14, 9981-9984
  •   Request permissions

    N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles

    J. A. Walker and L. M. Stanley, Org. Biomol. Chem., 2016, 14, 9981
    DOI: 10.1039/C6OB01956K

Search articles by author