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

GonzálezPelayo Silvia | Zendy; Bernardo Olaya | Zendy; Borge Javier | Zendy; López Luis A. | Zendy

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

Author(s) -

GonzálezPelayo Silvia,

Bernardo Olaya,

Borge Javier,

López Luis A.

Publication year - 2021

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.202001210

Subject(s) - chemistry , regioselectivity , sulfonyl , ruthenocene , metallocene , ferrocene , aryl , tetrahydroisoquinoline , aziridine , lewis acids and bases , isoquinoline , organic chemistry , combinatorial chemistry , polymer chemistry , ring (chemistry) , catalysis , alkyl , polymerization , polymer , electrode , electrochemistry

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.

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