While the synthetic utility of 1,3-cyclohexanediones has been thoroughly studied, comparatively little is known regarding the 1,2-cyclohexanedione system. Recent reports have shown that bicyclic adducts 5a  and 5b  result upon the reaction of 1,2-cyclohexanedione with �-nitrosyrenes in the presence of catalytic chiral bases. We have found that the use of stoichiometric achiral bases afford the adducts 3  and 4  . Based on this preliminary work, we are investigating the potential of this reaction to serve as a source of precursors for the preparation of a variety of fused ring heterocyclic systems. 

Michael additions of β-nitrostyrenes to 1,2-cyclohexanedione

243rd National Meeting (2012)

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