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The decarboxylative route to azomethine ylides. Mechanism of 1,3-dipole formation
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1987
Year
Carbon DioxideBiosynthesisEngineeringBiochemistryα-Amino AcidsNatural SciencesDiversity-oriented SynthesisOrganic ChemistryStereoselective SynthesisChemistryHeterocycle ChemistrySupramolecular ChemistrySynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringIntermediate Oxazolidin-5-one1,3-Dipole Formation
Evidence is presented that indicates that the decarboxylative route to azomethine ylides from both primary and secondary, cyclic and acyclic, α-amino acids involves an intermediate oxazolidin-5-one which loses carbon dioxide in a 1,3-dipolar cycloreversion reaction to generate an azomethine ylide stereospecifically.