Stereoselective synthesis of 2,3-difunctionalised thioesters using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes |
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Authors: | Evans Lyndsay Ann Adams Harry Barber Christopher G Caggiano Lorenzo Jackson Richard F W |
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Affiliation: | Department of Chemistry, Dainton Building, The University of Sheffield, Brook Hill, Sheffield, UK. |
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Abstract: | Stereoselective nucleophilic epoxidation of protected 3-amino and 3-hydroxy-substituted 1-arylthio-1-nitroalkenes, followed by intramolecular capture involving the amino and hydroxyl protecting groups, has led to the formation of isomeric oxazolidinones 5 and 7, and a cyclic carbonate 11. Together with the oxazolidinone precursor anti-alpha-bromo thioester 15a, the absolute and relative stereochemistry of these compounds has been determined by X-ray crystallography. |
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