Synthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S-oxides
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A series of amino acid-derived chiral benzylthio alcohols have been prepared and characterised. A chiral mercapto alcohol derived from S-leucine has been used to form three chiral 2,4-disubstituted 1,3-oxathiolanes. One of these has been oxidised to the S-oxide and another to the S,S-dioxide. The cis and trans isomers have been characterised by 1H NMR in each case and it appears that thermal epimerisation at C-2 is possible at the sulfoxide oxidation state. The X-ray structure of major trans diastereomer of 2-phenyl-4-isobutyl-1,3-oxathiolane S,S-dioxide shows an envelope conformation with oxygen at the flap and an internal angle at sulfur of just 93.8°. This compound fragments upon flash vacuum pyrolysis at 700 °C to give SO2, benzaldehyde and 4-methylpent-1-ene.
Aitken , R A , Lightfoot , P & Thomas , A W 2020 , ' Synthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S -oxides ' , Journal of Sulfur Chemistry , vol. 41 , no. 4 , pp. 369-387 . https://doi.org/10.1080/17415993.2020.1754418
Journal of Sulfur Chemistry
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