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The Acylation of β-Keto Ester Dianions
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1974
Year
BiosynthesisBioorganic ChemistryEngineeringBiochemistryNatural SciencesBiocatalysisOrganic ChemistryMethyl AcetoacetateSuccessful AcylationStereoselective Synthesisδ-Diketo EstersEnzymatic Modificationβ-Keto Ester DianionsSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
A method for the successful acylation of the dianion of simple β-keto esters to yield β,δ-diketo esters has been developed. The dianion of methyl acetoacetate also reacts with the monoanion of methyl acetoacetate to give a triketo ester which cyclizes to methyl orsellinate. These dianions also add to nitriles to give 5-amino-3-keto-4-pentenoates which may in some cases cyclize to 4-hydroxypyridones.