Synthesis of Metallocene Analogues of the Phenethylamine and Tetrahydroisoquinoline Scaffolds via Regioselective Ring Opening of 2-Aryl-N-sulfonyl Aziridin

Abstract

The Lewis (or Bronsted) acid-catalyzed reaction of 2-aryl-N-sulfonyl aziridines with ferrocene and ruthenocene provided new amino-functionalized metallocene derivatives arising from a regioselective ring opening of the aziridine. The functionalized metallocene derivatives available by this methodology are suitable precursors for the stereoselective synthesis of metallocene analogues of the relevant tetrahydroisoquinoline motif by a Pictet-Spengler type reaction. These isoquinoline analogues are also accessible by a TfOH-catalyzed three-component reaction of 2-aryl-N-sulfonyl aziridines, ferrocene (or ruthenocene) and formaldehyde.