Angewandte Chemie · 2015 · 55 citations · 89 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCatalyst DesignCatalyst PreparationCatalyst SynthesisOrganic SynthesisRedox CatalysisAsymmetric CatalysisAtom Economy In Coupling ReactionsEnantioselective CatalysisEnantioselective OxidationEnantioselective SynthesisReaction Mechanism ElucidationThiol Chemistry
Abstract A highly regio‐ and enantioselective hydrothiolation of terminal allenes, a reaction which fulfills the criteria of atom economy, is reported. Applying two chiral rhodium catalyst systems, a wide variety of thiols and allenes could be coupled. Oxidation gave access to the corresponding allylic sulfones in essentially enantiomerically pure form. The reaction tolerates a variety of functional groups and labeling experiments gave first insights into the reaction mechanism of this new methodology.
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