Resolution and absolute configuration of enantiomeric spiro-λ4-sulfane-precursor diaryl sulfoxides

Dénes Szabó, Szilárd Szendeffy, István Kapovits, Árpád Kucsman, Gyula Argay, Alajos Kálmán, Laśzló Párkányi

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6 Citations (Scopus)

Abstract

The spiro-λ4-sulfane (spirosulfurane) precursors 2-[(2-hydroxymethylphenyl)-sulfinyl]benzoic acid 1, 8-[(2-hydroxymethylphenyl)sulfinyl]-1-naphthoic acid 2, and 2-[(8-hydroxymethyl-1-naphthyl)sulfinyl]benzoic acid 3 were prepared from the corresponding sulfides by oxidation with chloramine-T. By using chiral organic bases racemic 1-3 were resolved to yield the enantiomers in high enantiomeric excess. The molecular structures of sulfoxides (+)-1, (+)-2, and (+)-3 were determined by X-ray diffraction method, and the absolute configuration of the stereogenic sulfur atom was assigned as (R), (S), and (S), respectively. The actual conformations are discussed including effective S···O close contacts and the relative positions of aromatic rings. Relevant bond lengths, angles and CD spectra are also given.

Original languageEnglish
Pages (from-to)2403-2410
Number of pages8
JournalTetrahedron Asymmetry
Volume8
Issue number14
DOIs
Publication statusPublished - Jul 24 1997

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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