STEREOSELECTIVE SYNTHESIS OF ISOQUINUCLIDINONES BY DIRECT IMINO-DIELS-ALDER TYPE REACTION CATALYZED BY L-PROLINE

摘要

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%).