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.