Stereoselective synthesis of 2,3-difunctionalised thioesters using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes.
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.
Evans
Lyndsay Ann
LA
Department of Chemistry, Dainton Building, The University of Sheffield, Brook Hill, Sheffield, UK.
Adams
Harry
H
Barber
Christopher G
CG
Caggiano
Lorenzo
L
Jackson
Richard F W
RF
D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis*; D023303:Oxazolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D000596:Amino Acids; D004852:Epoxy Compounds; D004952:Esters; D023303:Oxazolidinones