Multicomponent domino reaction from beta-ketoamides: highly efficient access to original polyfunctionalized 2,6-diazabicyclo[2.2.2]octane cores

Frédéric Liéby-Muller; Thierry Constantieux; Jean Rodriguez

doi:10.1021/ja055885z

Multicomponent domino reaction from beta-ketoamides: highly efficient access to original polyfunctionalized 2,6-diazabicyclo[2.2.2]octane cores

J Am Chem Soc. 2005 Dec 14;127(49):17176-7. doi: 10.1021/ja055885z.

Authors

Frédéric Liéby-Muller¹, Thierry Constantieux, Jean Rodriguez

Affiliation

¹ Université Paul Cézanne (Aix-Marseille III), CNRS UMR 6178, SYMBIO, Faculté des Sciences et Techniques, Case D12-13397, Marseille Cedex 20, France.

PMID: 16332052
DOI: 10.1021/ja055885z

Abstract

We describe a new multicomponent domino reaction from beta-ketoamides, involved as substrates and as nucleophilic partners. We obtain highly functionalized and original 2,6-diazabicyclo[2.2.2]octane cores (2,6-DABCO) in a five-step one-pot sequence, which is fast, environmentally friendly, operationally simple to manage, and combines step- and atom-economic aspects.