124652-18-2Relevant articles and documents
Synthesis and Characterisation ot Diastereomeric (4S)-3-Acetyl-2-aryl-5,5-dimethyl-4-thiazolidinecarboxylic Acids
Gyoergydeak, Zoltan,Kajtar, Judit,Kajtar, Marton,Kajtar-Peredy, Maria
, p. 281 - 286 (2007/10/02)
The condensation of aromatic aldehydes 1 and D-penicillamine (2) in aqueous methanol gives (4S)-2-aryl-5,5-dimethyl-4-thiazolidinecarboxylic acids 3 with alternating diastereoselectivity in position 2.Acetylation of the products with acetic anhydride in pyridine or in water gives rise to (2S,4S)-3-acetyl-2-aryl-5,5-dimethyl-4-thiazolidinecarboxylic acids 5.Use of a HCl/dioxane system in the reaction of N-acetyl-D-penicillamine (6) with aldehydes made possible the effective preparation of (2R,4S) compounds 8.The diastereommeric compounds 5 and 8 were characterized by (1)H- and (13)C-NMR data and optical rotation and CD.The results were compared with those compiled from the already synthesized diastereomeric (4R)-3-acetyl-2-aryl-4-thiazolidinecarboxylic acids.