The stereospecific Fe-catalyzed arylation of enol tosylates was reported. Various tri- or tetrasubstituted Z or E-enol tosylates of β-keto esters were arylated using common and Knochel-type Grignard reagents with complete stereofidelity. The precursors for Z/E-zimelidine, tamoxifen and other bioactive compounds were facilely prepared without precious and toxic transition metals.
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Base-mediated synthesis of aryl enol ethers from α-aryl allylic alcohols and arylsulfonium salts.
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A concise synthesis of aryl enol ethers from allylic alcohols and arylsulfonium salts by simply using an inorganic base as a mediator is described. The reaction enabled the facile conversion of various α-aryl allylic alcohols into the corresponding aryl enol ethers in good yields with excellent selectivity. The results demonstrated that both symmetric triarylsulfonium triflate and 10-methyl-5-aryl-5,10-dihydrophenothiazin-5-ium salts were effective arylation reagents for the base-initiated selective -arylation and isomerization of α-aryl allylic alcohols.
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