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A Practical Asymmetric Synthesis of Enantiomerically Pure 3-Substituted Pyroglutamic Acids and Related Compounds
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2000
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Room TemperatureSchiff BaseBiochemistryGlycine 1Natural SciencesOrganic ChemistryPractical Asymmetric SynthesisStereoselective SynthesisChemistryRelated CompoundsHeterocycle ChemistryPharmacologyAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisNatural Product Synthesis
DBU-catalyzed Michael addition reactions were shown to occur at room temperature between a nickel(II) complex of the Schiff base of glycine 1 and (S)- or (R)-N-(E-enoyl)-4-phenyl-3-oxazolidin-2-ones (2, see scheme). This reaction, which has an almost completely stereoselective outcome, provides a practical and generalized approach to a family of glutamic/pyroglutamic acids. R=alkyl, aryl. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2000/z14093_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.