Stereospecific synthesis and absolute configuration of optically active diaryl(acyloxy)(alkoxy)spiro-λ4-sulfanes

Dénes Szabó, Szilárd Szendeffy, István Kapovits, Árpád Kucsman, Mátyás Czugler, Alajos Kálmán, Péter Nagy

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Abstract

Optically active (R)-(+)-1,1'-spirobi[3H-2,1-benzoxathiol]-3-one (R)-(+)-5, the (R)-(+) and (S)-(-) enantiomers of spiro[3H-2,1-benzoxathiol-1,1'-naphtho[1,8-d,e]3H-2,1-oxathiin-3-one] (R)-(+)-8 and (S)-(-)-8, and (S)-(+)-spiro[3H-2,1-benzoxathiol-3-one-1,1'-naphtho[1,8-d,e]-3H-2,1-oxathiine] (S)-(+)-10 all belonging to the class of diaryl(acyloxy)-(alkoxy)spiro-λ4-sulfanes (spirosulfuranes) were prepared by dehydration of the optically active diaryl sulfoxides (R)-(+)-4, (R)-(-)-7, (S)-(+)-7, and (S)-(+)-9, respectively, all of them carrying reactive CH2OH and COOH substituents. (R)-(+)-5H,7H-dibenzo[c,f]-1,5-oxathiocin-5-one 12-oxide (R)-(+)-6, a sulfoxide-lactone isomer of spiro-λ4-sulfane (R)-(+)-5 was also obtained from (R)-(+)-4 by dehydration. The molecular structures including the absolute configurations were determined for (R)-(+)-5, (R)-(+)-6 and (R)-(+)-8 by X-ray diffraction method. Relevant bond length and angle data are listed. Sulfur configurations, solid-state conformations and a stereospecific pathway for the dehydration of sulfoxides are discussed in detail.

Original languageEnglish
Pages (from-to)2411-2420
Number of pages10
JournalTetrahedron Asymmetry
Volume8
Issue number14
DOIs
Publication statusPublished - Jul 24 1997

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ASJC Scopus subject areas

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

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