Organosilicon Reducing Reagents for Stereoselective Formations of Silyl Enol Ethers from α‑Halo Carbonyl Compounds


Salt-free stereoselective synthesis of silyl enol ethers was achieved by treating α-halo carbonyl compounds with 2,3,5,6-tetramethyl-1,4-bis­(trimethylsilyl)-1,4-dihydropyrazine. In this reaction, easily removable trimethylsilyl halides and 2,3,5,6-tetramethylpyrazine were generated as the reaction byproducts. Due to the inertness of the reaction byproducts, we found a one-pot transformation of the <i>in situ</i> generated silyl enol ethers into various α-functionalized carbonyls by reaction with Togni-II reagent or aldehydes

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