Enantioselective synthesis of bridged bicyclic ring systems

The type 2 intramolecular Diels-Alder (IMDA) reaction is a valuable method for synthesis of both carbocyclic and heterocyclic bridged bicyclo5.3.1]undecane and bicyclo4.3.1]decane ring systems. These structures are common to a number of biologically important natural products. Asymmetric variants of the type 2 IMDA reaction incorporating oxazolidinone chiral auxiliaries have been evaluated. This study has resulted in systems that deliver bridged bicyclic 5.3.1] and 4.3.1] ring systems in high diastereomeric (97-99% de) and enantiomeric purity.