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Darstellung und Charakterisierung von diastereomeren (4S)-3-Acetyl-2-aryl-5,5-dimethyl-4-thiazolidincarbonsäuren

✍ Scribed by Györgydeák, Zoltán ;Kajtár, Judit ;Kajtár, Márton ;Kajtár-Peredy, Mária

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
612 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Synthesis and Characterisation of Diastereomeric (4__S__)‐3‐Acetyl‐2‐aryl‐5,5‐dimethyl‐4‐thiazolidinecarboxylic Acids

The condensation of aromatic aldehydes 1 and D‐penicillamine (2) in aqueous methanol gives (4__S__)‐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 (2__S__,4__S__)‐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 (2__R__,4__S__) compounds 8. The diastereomeric 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 (4__R__)‐3‐acetyl‐2‐aryl‐4‐thiazolidinecarboxylic acids.

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