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

Z. Györgydeák, Judit Kajtár, Márton Kajtár, M. Kajtár-Peredy

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Synthesis and Characterisation of Diastereomeric (4S)‐3‐Acetyl‐2‐aryl‐5,5‐dimethyl‐4‐thiazolidinecarboxylic Acids 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 diastereomeric compounds 5 and 8 were characterized by 1H‐ and 13C‐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.

Original languageGerman
Pages (from-to)281-286
Number of pages6
JournalLiebigs Annalen der Chemie
Volume1990
Issue number3
DOIs
Publication statusPublished - 1990

Keywords

  • Thiazolidine, 4‐carboxylic acid

ASJC Scopus subject areas

  • Medicine(all)

Cite this

Darstellung und Charakterisierung von diastereomeren (4S)‐3‐Acetyl‐2‐aryl‐5,5‐dimethyl‐4‐thiazolidincarbonsäuren. / Györgydeák, Z.; Kajtár, Judit; Kajtár, Márton; Kajtár-Peredy, M.

In: Liebigs Annalen der Chemie, Vol. 1990, No. 3, 1990, p. 281-286.

Research output: Contribution to journalArticle

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