Asymmetric Cyanosilylation of α‐Keto Esters Catalyzed by the [Ru(phgly)2(binap)]–C6H5OLi System

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AbstractThe asymmetric reaction of α‐keto esters and (CH3)3SiCN, catalyzed by a combined system of [Ru{(S)‐phgly}2{(S)‐binap}] and C6H5OLi with a substrate‐to‐catalyst molar ratio (S/C) of 1000 at –60 °C, affords silylated cyanohydrins in up to 99 % ee. Cyanosilylation smoothly proceeds with an S/C of 10,000 at –50 °C. The use of Xyl‐Binap instead of Binap as a ligand provides better enantioselectivity in some cases. A series of aromatic, hetero‐aromatic, aliphatic, and α,β‐unsaturated keto esters are converted into the desired products.