Enantioselective Asymmetric Michael Addition of Cyclic Diketones to β,γ‐Unsaturated α‐Keto Esters

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AbstractAn efficient, organocatalytic enantioselective addition of cyclic diketones with β,γ‐unsaturated α‐keto esters has been developed that affords products in high yields (up to 95 %) and excellent enantioselectivity (up to >99 % ee) under mild conditions with a low catalyst loading (2.5 mol‐%). The unsaturated α‐keto esters are effectively coordinated and activated through hydrogen bonds with the squaramides and proved to be excellent hydrogen‐bond acceptors in this asymmetric organocatalytic reaction. This reaction provides valuable and easy access to chiral Michael adducts, which are important moieties in the skeletons of biological and pharmaceutical molecules.