Synthesis of Oxazolidinones by using Carbon Dioxide as a C1 Building Block and an Aluminium-Based Catalyst

Mani Sengoden, Michael North*, Adrian C. Whitwood

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Oxazolidinone synthesis through the coupling of carbon dioxide and aziridines was catalysed by an aluminium(salphen) complex at 50–100 °C and 1–10 bar pressure under solvent-free conditions. The process was applicable to a variety of substituted aziridines, giving products with high regioselectivity. It involved the use of a sustainable and reusable aluminium-based catalyst, used carbon dioxide as a C1 source and provided access to pharmaceutically important oxazolidinones as illustrated by a total synthesis of toloxatone. This protocol was scalable, and the catalyst could be recovered and reused. A catalytic cycle was proposed based on stereochemical, kinetic and Hammett studies.

Original languageEnglish
JournalChemSusChem
Early online date26 Jun 2019
DOIs
Publication statusE-pub ahead of print - 26 Jun 2019

Bibliographical note

© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.


author accepted manuscript publisher on 29 May 2019

Keywords

  • aluminium catalysis
  • aziridines
  • carbon dioxide fixation
  • oxazolidinones
  • Schiff bases

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