Published January 1, 2014
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Synthesis of gamma,delta-Aziridino alpha-Amino Acid Derivatives and their Stereoselective Ring Transformation to 2-(Aminomethyl)-1-aminocyclopropanecarboxylic Acid Derivatives
Creators
- 1. Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, B-9000 Ghent, Belgium
- 2. Mersin Univ, Fac Pharm, Dept Chem, TR-33169 Mersin, Turkey
- 3. Univ Antwerp, Dept Med Chem, B-2610 Antwerp, Belgium
- 4. Univ Bergen, Dept Chem, N-5007 Bergen, Norway
Description
1-Benzyl-2-(bromomethyl)aziridine was successfully substituted with protected glycine esters to afford alkyl 3-(N-benzylaziridin-2-yl)-2-aminopropanoates, as constrained heterocyclic diamino acid derivatives, in good isolated yields. These new aziridines proved to be excellent building blocks for ring transformation to the corresponding stereochemically defined 2-(aminomethyl)-1-aminocyclopropanecarboxylic acid derivatives, including methyl esters, piperidyl amides, and free carboxylic acids.
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