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Enantiospecific, Stereoselective Synthesis of Enantiomerically Pure Aziridine-2-carboxylic Acids from Aspartic Acid
Published: 01 November 1998 by MDPI in The 2nd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: Enantiomerically pure aziridine-2-carboxylates containing a CH2OMs group, and azetidine-3-mesyloxy-2- carboxylates were prepared by cyclization of 2-amino-3,4-dimesyloxybutyrates, stereoselectiveprepared from aspartic acid. The outcome of the cyclization was dictated by the configuration of the C-3 stereogenic center. The mesylate group of the aziridino mesylates could be displaced by nucleophiles without opening of the aziridine ring.
Keywords: Aziridine-2-carboxylic acids, azetidine-2carboxylic acids, aziridine ring formation, azetidine ring formation.