Liebigs Annalen der Chemie · 1994 · 20 citations · 12 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryOrganometallic ChemistrySynthetic Medicinal ChemistryCarboxylic AcidsCarboxylic DerivativesHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisAsymmetric Heterocycle SynthesisAsymmetric SynthesisAzetidine ChemistryCarboxylic Acid Derivative SynthesisCarboxylic Acid FormationCarboxylic Acid Synthesis
Chemistry of Aziridine Carboxylic Acids, V. – Asymmetric Synthesis of Enantiomerically Pure Aziridine Carboxylic Acid Derivatives from ( R )‐ and ( S )‐Glyceraldehyde Acetonide The α‐bromoacrylic acid derivatives 2 reacted with benzylamine by ring closure to cis ‐aziridines 3 and trans ‐aziridines 4 with ≥99% diastereomeric excess. The aziridines 3 and 4 were hydrogenated by LiAlH 4 to give alcohols 5 and 6 . Tosylations of 6 yielded the crystalline sulfonamides 7 . The absolute configurations of (2 R ,3 S ,4 R )‐ 3c , (2 S ,3 R ,4 S )‐ 5 and (1 R ,2 R ,4 R )‐ 7 were determined by X‐ray analyses.
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