Resolution and absolute configuration of enantiomeric spiro-λ4-sulfane-precursor d diaryl sulfoxides
作者： Dénes Szabó , Szilárd Szendeffy , István Kapovits , Árpád Kucsman , Gyula Argay
DOI: 10.1016/S0957-4166(97)00244-9
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摘要: Abstract The spiro-λ4-sulfane (spirosulfurane) precursors 2-[(2-hydroxymethylphenyl)-sulfinyl]bezoic acid 1, 8-[(2-hydroxymethylphenyl)sulfinyl]-1-naphthoic 2, and 2-[8--hydroxymethyl-1-naphthyl)sulfinyl]benzoic 3 were prepared from the corresponding sulfides by oxidation with chloramine-T. By using chiral organic bases racemic 1–3 resolved to yield enantiomers in high enantiomeric excess. molecular structures of sulfoxide (+)-1, (+)-2, (+)-3 determined X-ray diffraction method, absolute configuration stereogenic sulfur atom was assigned as (R), (S), respectively. actual conformations are discussed including effective S…O close contacts relative positions aromatic rings. Relevant bond lengths, angles CD spectra also given.
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