Organocatalytic Asymmetric Synthesis of Biologically Relevant 3,3- Dihydroxyphenyloxindoles via para-Quinone Methides Derived from Isatins

The first asymmetric synthetic approach to biologically relevant 3,3-diphenyloloxindoles was developed using para-quinone methides derived from isatins and phenols. Chiral phosphoric acid efficiently catalyzed the reaction and delivered 3,3-diphenyloloxindoles under mild conditions with up to an equivalent yield and excellent enantioselectivity (up to >99% ee). The chirality was maintained in further synthesis.