Abstract
(S )-(+)-3-(p -Tolylsulfinyl)furan-2(5H )-one and (S )-(+)-3-(p -tolylsulfinyl)-5,6-dihydropyran-2-one
can be synthesized by a new and significantly improved method consisting
of Knoevenagel condensation of benzyl (R )-(+)-(p -tolylsulfinyl)acetate with the tert -butyldimethylsilyl derivatives of
2-hydroxyacetaldehyde or 3-hydroxypropanal, followed by subsequent
reactions of the resulting mixtures with hydrogen in the presence
of palladium-on-carbon and ethereal hydrogen chloride.
Key words
asymmetric synthesis - chiral auxiliaries - sulfoxides - α,β-unsaturated lactones - butenolides
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8 mmol scale) overall yield, respectively.
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as chiral shift reagent.
