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Catalytic intermolecular alkene oxyamination with nitrenes. | LitMetric

Catalytic intermolecular alkene oxyamination with nitrenes.

Chemistry

Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France).

Published: July 2014

AI Article Synopsis

  • The Rh(II) catalyst effectively promotes the addition of nitrenes to alkenes, producing vicinal amino alcohols with high yields (up to 95%) and full regioselectivity.
  • This process, known as 1,2-oxyamination, forms an aziridine intermediate that subsequently opens its ring.
  • The ring opening is facilitated by the Rh-bound nitrene, which acts as a Lewis acid in the reaction.

Article Abstract

The Rh(II)-catalyzed intermolecular addition of nitrenes to aromatic and aliphatic alkenes provides vicinal amino alcohols with yields of up to 95 % and complete regioselectivity. This 1,2-oxyamination reaction involves the formation of an aziridine intermediate that undergoes in situ ring opening. The latter is induced by the Rh-bound nitrene that behaves as a Lewis acid.

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Source
http://dx.doi.org/10.1002/chem.201400301DOI Listing

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