Synthesis of Butenolides from α-(Phenylthio)-ketones and -esters: Crystal Structure of an Intermediate β-Phenylthio-γ-lactone

DOI: 10.1039/P19810002751

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2751 - 2759 (1981)

Update date:2022-09-26

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Authors:

Brownbridge, Peter

Egert, Ernst

Hunt, Paul G.

Kennard, Olga

Warren, Stuart

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Article abstract of DOI:10.1039/P19810002751

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 Δ^αβ-butenolides.Treatment of 5,5-dimethyl-4-oxo-3-(phenylthio)-hexanoic acid with NaBH4 gives a single γ-lactone whose PhS and Bu^t groups are shown to be cis by X-ray crystal structure determination.

Full text of DOI:10.1039/P19810002751

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