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Prostereogenic Face and Orientation Selective Oxidative Coupling Reaction between Methyl Methacrylate and 2,5-Dihydrofuran Catalyzed by a Ruthenium(0) Compound

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journal contribution
posted on 28.03.2011, 00:00 by Yuki Hiroi, Nobuyuki Komine, Masafumi Hirano, Sanshiro Komiya
We disclose the first prostereogenic face and orientational control of coordinated olefins in an oxidative coupling reaction at a transition-metal center. Chemo-, regio-, and diastereoselective cross-dimerization between methyl methacrylate (MMA) and 2,5-dihydrofuran is catalyzed by Ru(η6-naphthalene)(η4-1,5-COD) (1; 5 mol %) at 0 °C in 24 h without use of solvent to give methyl rac-(2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methylpropionate (2a) in 81% yield.