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Enantiomerically Pure Aziridine-2-carboxylates and Their Derivatives for Organic Synthesis

Preparation of Enantiomerically Pure Aziridine-2-carboxylates


Transformation of the Side Chain Attached to the Chiral Aziridine

   Preparation of 2-acylaziridines

   Stereoselective reduction of 2-acylaziridines to provide vicinal amino alcohols

   Stereoselective additions to the aldimine

   Preparation of 2-vinylaziridines


Aziridine Ring-opening

   Regioselective reductive ring-opening


   Regioselective ring-opening with heteroatom nucleophiles

     - with oxygen


     - with nitrogen and sulfur



   Summary


Rearrangements and ring expansions

   Preparation of 5-functionalized oxazolidinones


   Preparation of 4-functionalized oxazolidinones


Asymmetric synthesis of amino acid derivatives from chiral aziridines

   Representative examples

 

Both (2R)- and (2S)-aziridine-2-carboxylates and their derivatives are now commercially available in bulk quantities in optically pure forms. Stereo- and regioselective transformations including aziridine ring-opening reactions enable us to prepare a variety of nitrogen-containing molecules. Some of them may be useful in the practical synthesis of commercially valuable compounds and as starting molecules to generate diverse compound libraries.

 

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