Diastereoselective Azidations of (S)-4-Carboethoxymethyloxazolidin-2-one for 4-Oxy-2,3-diaminobutanoates

Vicinal diamine moiety has been found in diverse classes of biologically active compounds including antibiotics, anti-fungal dipeptides, and alkaloids.1 Also, recent advance in asymmetric synthesis requires more practical route to enantiopure vicinal diamine derivatives for use as chiral auxiliaries or metal ligands of asymmetric catalysts.2 In the synthesis of peptidomimetics for rational design of a therapeutic agent, α,β-diamino acids can be employed to establish the optimum conformation and the binding site of a protein for high binding affinity and selectivity against a target protein. Several methods for α,β-diaminobutanoic acid, the simplest α,β-diamino acid present as a key structural element of the known natural products, have been reported. These methods include Mitsunobu reaction of threonine for the introductio