Molecules 2000, 5(3), 293-298; doi:10.3390/50300293
Article

Aziridine Carboxylates, Carboxamides and Lactones: New Methods for Their Preparation and Their Transformation into α- and β-Amino Acid Derivatives

Published: 22 March 2000
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The preparation of a variety of novel aziridine-γ-lactones (3) from carbohydrates is described. In contrast to aziridine-2-carboxylates, the lactones react regiospecifically at C-2 with soft nucleophiles to provide optically pure substituted β-amino acid precursors. Hard nucleophiles react exclusively at the C-3 position to provide α-amino acid precursors. The utility of this methodology was demonstrated by the preparation of (3S,4S)-dihydroxy-L-glutamic acid (DHGA) from the appropriate aziridine-γ-lactone. DHGA was subsequently shown to be a selective partial agonist of mGluR1 receptors. A more concise preparation of aziridine-γ-lactones was achieved by 1,4-Michael addition of benzylamine to 2-O-triflylbutenolides. Use of a 2-O-mesylbutenolide led, under the same conditions, to the corresponding aziridine-2-carboxamides or 2-carboxylates. Finally, a new Evanstype aziridinating agent, Ses-iminoiodinane, was developed and shown to react efficiently with unsaturated substrates to give the corresponding aziridines, whose N-Ses protecting groups can be removed under mild conditions.
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MDPI and ACS Style

Dodd, R.H. Aziridine Carboxylates, Carboxamides and Lactones: New Methods for Their Preparation and Their Transformation into α- and β-Amino Acid Derivatives. Molecules 2000, 5, 293-298.

AMA Style

Dodd RH. Aziridine Carboxylates, Carboxamides and Lactones: New Methods for Their Preparation and Their Transformation into α- and β-Amino Acid Derivatives. Molecules. 2000; 5(3):293-298.

Chicago/Turabian Style

Dodd, Robert H. 2000. "Aziridine Carboxylates, Carboxamides and Lactones: New Methods for Their Preparation and Their Transformation into α- and β-Amino Acid Derivatives." Molecules 5, no. 3: 293-298.

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