A general and mild catalytic allylation of carbonyl compounds, applicable to aldehydes, ketones, and imines is developed using allyltrimethoxysilane as the allylating reagent. The reaction proceeds smoothly with 1-10 mol % of CuCl and TBAT in THF at ambient temperature. Mechanism studies indicated that the copper alkoxide, allylfluorodimethoxysilane, and allyltrimethoxysilane are essential to promote the reaction efficiently. Preliminary extension of the reaction to the first catalytic enantioselective allylation of ketones using an allylsilane produced the product with 61% ee from acetophenone, using a CuCl-p-tol-BINAP-TBAT catalyst (15 mol %).

Chiral ketone cyanohydrins are important and versatile synthetic intermediates, which can be easily converted to R-hydroxy carbonyl compounds that contain chiral quaternary stereocenters. 1,2 Recently, we have developed a novel chiral ligand 1 derived from D-glucose and found that the Ti-1 complex catalyzes a highly

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