Journal
CHEMSUSCHEM
Volume 12, Issue 14, Pages 3296-3303Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201901171
Keywords
aluminium catalysis; aziridines; carbon dioxide fixation; oxazolidinones; Schiff bases
Funding
- Science & Engineering Research Board [SB/OS/PDF-092/2016-17]
- New Delhi, India
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Oxazolidinone synthesis through the coupling of carbon dioxide and aziridines was catalysed by an aluminium(salphen) complex at 50-100 degrees 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 C-1 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.
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