An Enantioselective Organocatalytic Oxidative Dearomatization Strategy

We have developed a catalytic enantioselective strategy for chemical synthesis wherein flat aromatic molecules are directly converted to complex nonracemic molecular architectures. The process involves oxidative dearomatization of substituted phenols followed by a desymmetrizing secondary amine-catalyzed asymmetric intramolecular Michael addition and reveals a decalin structure, formed with exquisite control of three new stereogenic centers and an array of exploitable orthogonal functionality, directly from a flat molecule that is devoid of architectural complexity.