Chiralnon-racemic bicyclic lactams have been utilized as scaffolds in thestereoselective synthesis of a number of heterocyclic systems.  The application of an acyliminium ionstrategy to 5,5,6-tricyclic lactams has the potential to provide direct accessto chiral phthalazinone, bicyclic pyrrolidone and bicyclic pyrrole systems ifone can avoid the acyliminium ion � enamine equilibration that compromises thestereoselectivity of reaction.  Inthis presentation the stereoselective cyclocondensation of amino alcohols and2-keto cyclohexanoic acids and the subsequent stereoselective conversion to phthalazinone,pyrrolidone and pyrrole systems via acyliminium ions will be presented.

Acyliminium ion chemistry of 5,5,6-tricyclic lactams

239th National Meeting (2010)

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