[n + 1] Annulation Route to Highly Substituted Cyclic Ketones with Pendant Ketone, Nitrile, and Ester Functionality

Two carbon acids connected by a tether containing a ketone undergo two Michael reactions to 3-butyn-2-one to afford highly substituted and functionalized cyclic ketones with pendant ketone, nitrile, and ester functionality. The stereochemical courses of the double Michael reactions vary remarkably with the structure of the starting material. Double Michael adducts with equatorially disposed cyano groups can be hydrogenated to afford trans-fused bicyclic amines.