Synthesis of butenolides from α-(phenylthio)-ketones and -esters: crystal structure of an intermediate β-phenylthio-γ-lacton
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2751-2759
- https://doi.org/10.1039/p19810002751
Abstract
Alkylation of α-(phenylthio)-ketones or -esters with iodoacetate anion gives 1,4-dicarbonyl compounds which are reduced stereoselectively to β-phenylthio-γ-butyrolactones. Oxidation to sulphoxides and thermolysis provides a general synthesis of β- and γ-substituted Δαβ-butenolides. Treatment of 5,5-dimethyl-4-oxo-3-(phenylthio)-hexanoic acid with NaBH4 gives a single γ-lactone whose PhS and But groups are shown to be cis by an X-ray crystal structure determination.Keywords
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