Cinchona alkaloid-derived chiral quaternary ammonium organocatalysts were developed. The catalyst with a bulky 1-adamantoyl group at the C-9 position promoted the enantioselective 伪-hydroxylation of 尾-oxo esters and resulted in the corresponding products in 35鈥?5% yields and 58鈥?0% ee. The reaction was successfully scaled to a gram-quantity scale with a similar yield without loss of enantioselectivity.