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

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 methodolo...

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Bibliographic Details
Authors: González-Pelayo, Silvia, López García, Luis Ángel, Bernardo, Olaya, Borge, Javier
Format: article
Publication Date:2020
Country:España
Institution:Universidad de Salamanca (USAL)
Repository:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:gredos.usal.es:10366/154732
Online Access:http://hdl.handle.net/10366/154732
Access Level:Open access
Keyword:CyclizationMetallocenesMulticomponent reactionsNitrogen heterocyclesStrained molecules
Description
Summary: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.

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