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Organocatalytic Cyclization of COS and Propargylic Derivatives to Value‐Added Heterocyclic Compounds

The organocatalytic cyclization of propargylic amines/amides with carbonyl sulfide (COS) was firstly achieved by employing COS adducts of Lewis base (LB) as organocatalysts, affording various functionalized 1,3‐thiazolidine‐2‐ones, and 1,3‐thiazolidine‐2,4‐diones derivatives in a highly chemo‐ and stereoselective manner. The isotope labeling and stoichiometric experiments suggested the LB‐COS adducts preferentially mediated basic ionic pair mechanism. Furthermore, the practical application of this methodology was highlighted by the highly efficient synthesis of rosiglitazone using COS as sulfur source.