期刊
CHEMCATCHEM
卷 11, 期 23, 页码 5728-5732出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201900490
关键词
organocatalysis; carbonyl sulfide; cyclization; 1; 3-thiazolidine-2-one; 1; 3-thiazolidine-2; 4-dione
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.
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