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Abstract
AbstractAn effective method for the asymmetric synthesis of 5‐hydrazinothiazol‐4‐one‐5‐carboxylates was developed. The tetrasubstituted chiral carbon center was generated by asymmetric amination of thiazol‐4‐one‐5‐carboxylate with azodicarboxylate catalyzed by a bifunctional squaramide‐based (1R,2R)‐cyclohexane‐1,2‐diamine backbone in good to excellent yields (40–96%) with high levels of enantioselectivity (92–98% ee). A representative transformation of the amination product to a biologically important 1,3,4‐oxadiazol‐2(3H)‐one is achieved without any appreciable loss in enantioselectivity. Additionally, upon treatment with NaBH3CN, the amination product could also be converted into a biologically important thiazolidin‐4‐one derivative in good yield without any loss of stereochemical integrity.
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