Synthesis of Metallocene Analogues of the Phenethylamine and Tetrahydroisoquinoline Scaffolds via Regioselective Ring Opening of 2‐Aryl‐N‐sulfonyl Aziridines.

The Lewis (or Brønsted) 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. [ABSTRACT FROM AUTHOR]