Journal of the Chemical Society. Perkin transactions I p. 2751 - 2759 (1981)
Update date:2022-09-26
Topics:
Brownbridge, Peter
Egert, Ernst
Hunt, Paul G.
Kennard, Olga
Warren, Stuart
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 X-ray crystal structure determination.
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Doi:10.1021/acs.joc.9b00683
(2019)Doi:10.1016/S0008-6215(00)80526-1
(1981)Doi:10.1055/s-1982-29825
(1982)Doi:10.1021/jo00343a014
(1982)Doi:10.1007/s10593-008-0013-9
(2008)Doi:10.1016/S0040-4020(01)92542-6
(1966)
