An expeditious synthesis of cyanohydrin trimethylsilyl ethers using tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst

Phthalimide and tetraethylammonium hydroxide react via ail unusual pathway to afford tetraethylammonium 2-(carbamoyl)benzoate (TEACB) which is of interest as a bifunctional organocatalyst. TEACB (0.5 mol %) was found to catalyze the addition of trimethylsilyl cyanide (TMSCN) to carbonyl compounds under solvent-free conditions at room temperature with very short reaction times. A wide variety of aldehydes and ketones were transformed into the corresponding cyanohydrin trimethylsilyl ethers in high to quantitative yields. (C) 2009 Elsevier Ltd. All rights reserved.