Catalytic Enantioselective Dearomatization/Rearomatization of 2-Nitroindoles to Access 3-Indolyl-3'-Aryl-/Alkyloxindoles: Application in the Formal Synthesis of Cyclotryptamine Alkaloids.

ABSTRACT

The first catalytic enantioselective dearomatization/rearomatization of 2-nitroindoles triggered by the Michael addition of 3-monosubstituted oxindoles was established. A wide range of 3-indolyl-3'-alkyloxindoles (up to 99% yield, 97% ee) and 3-indolyl-3'-aryloxindoles (up to 95% yield, 99% ee) were obtained by using an organocatalyst. This method provides an unprecedented strategy to access structurally diverse 3,3'-disubstituted oxindoles bearing a sterically congested triaryl-containing all-carbon quaternary stereocenter. The utility of this approach was verified by the formal synthesis of cyclotryptamine alkaloids.