On the anomalous behaviour of (3RS,4RS)-[(2RS)-3-acetylthiazolidin-2-yl]-1-(4-methoxyphenyl)azetidin-2-ones towards cerium(IV) ammonium nitrate (CAN). An unprecedented oxidative ring transformation.

Ferenc Bertha, József Fetter, Mária Kajtár-Peredy, György M. Keseru, Károly Lempert, László Párkányi, József Tamás

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11 Citations (Scopus)

Abstract

Starting with (2RS,3RS)-1-(4-methoxyphenyl)-4-oxo-3-phthalimidoazetidine-2-carbaldehyde (1) the two diastereoisomeric 4-(3-acetylthiazolidin-2-yl)-1-(4-methoxyphenyl)-3-phthalimidoazetidin-2-ones 4a and 5a were prepared and converted into their 3-allyloxycarbonylamino analogues 4c and 5c, respectively. While the (3RS,4RS,2′SR) isomers 4a and 4c were readily N-deprotected with cerium (IV) ammonium nitrate (CAN) to yield the expected 6a and 6c, respectively, treatment of the (3RS,4RS,2′RS) isomers 5a and 5c with CAN led to compounds 7a and 7c, respectively, via oxidative ring transformation. The structure of compound 7a was established by an X-ray diffraction study. A rationale, based on AM1 and MMX calculations is given for the dissimilar behaviour of the diastereoisomers.

Original languageEnglish
Pages (from-to)7803-7822
Number of pages20
JournalTetrahedron
Volume49
Issue number35
DOIs
Publication statusPublished - Aug 17 1993

Keywords

  • AM1 and MMX Calculations
  • Oxidative Ring Transformation
  • Relative Configuration and Reactivity
  • X-Ray Molecular Structure Determination
  • β-Lactams

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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