European Journal of Organic Chemistry · 2004 · 22 citations · 51 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryAddition ReactionsCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisConjugate AdditionElectrophilic CatalysisElectrophilic ReactivityStereoselectivity In Addition ReactionsThiol ChemistryThiol FunctionalizationThiol Substitution ReactionsThiols Protecting Groups
Abstract Several new 4‐thio‐4,5‐dihydro‐2(3 H )‐furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5 H )‐furanones. When 5‐methyl‐2(5 H )‐furanone was used as the electrophilic substrate, the reaction was diastereoselective affording exclusively the cis ‐α,β‐disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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