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Synthesis of (Z)-Cinnamate Esters by Nickel-Catalyzed Stereoinvertive Deoxygenation of trans-3-Arylglycidates

We report a stereoinvertive deoxygenation of trans-3-arylglycidates as an alternative route to access thermodynamically less stable (Z)-cinnamate esters by using nickel triflate and triphenylphosphine. Broad functional-group tolerance was observed, with trans-3-arylglycidates containing methyl, methoxy, halo, or nitro groups affording the corresponding (Z)-cinnamate esters in high yields and with moderate to high E/Z ratios.