One-Pot Quinine-Catalyzed Synthesis of α-Chiral γ-Keto Esters: Enantioenriched Precursors of cis-α,γ-Substituted-γ-Butyrolactones

A highly enantioselective one-pot synthesis of important building blocks, α-chiral γ-keto esters, has been developed by combining a quinine-catalyzed Michael addition of malononitrile to trans-enones followed by magnesium monoperoxyphthalate (MMPP) oxidation. These synthons proved to be useful reagents for a simple access to challenging cis-α,γ-disubstituted γ-butyrolactones in good diastereoselectivity and high enantiocontrol. (Figure presented.)