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Paper | Regular issue | Vol 78, No. 12, 2009, pp.2963-2978
Published online, 15th September, 2009
DOI: 10.3987/COM-09-11797
Stereoselective Synthesis of Isoquinuclidinones by Direct Imino-Diels-Alder Type Reaction Catalyzed by L-Proline

Noelia Quiñones, Fernándo Aznar,* and María-Paz Cabal

*instituto Universitario de Química Organometálica "Enrique Moles", Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33071- Oviedo, Spain

Abstract

A general synthesis of isoquinuclidinones (2-azabicyclo[2.2.2]octan-5-ones), has been developed by one-pot three component imino-Diels-Alder type reaction catalyzed by L-proline. Simple and commercially available α,β-unsaturated cyclic ketones, aromatic aldehydes and either aliphatic or aromatic primary amines were used. The reaction proceeds with excellent exo-diastereoselectivity (>99%) and moderated enantioselectivity (30-64%).