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A Convenient Way for the Conversion of Carboxylic Esters into 2-Substituted Allyl Halides
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2005
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Cross-coupling ReactionEngineeringAlkene Metathesis2-Substituted Allyl HalidesRequired Allyl BromidesConvenient WayOrganic ChemistryCatalysisStereoselective SynthesisChemistryCarboxylic EstersAsymmetric CatalysisHalide DisplacementEnantioselective SynthesisBiomolecular Engineering
The preparation of functionalized 2-substituted allyl bromides and chlorides from carboxylic esters is reported. The carboxylic esters were transformed first to 1-substituted cyclopropanols by treating with ethylmagnesium bromide in the presence of titanium alkoxide. Mesylation of the cyclopropanols followed by halide displacement of the sulfonate group to halogen, accompanied by cyclopropyl-allyl rearrangement, affords the required allyl bromides and chlorides.