Dynamic kinetic resolution of hemiaminals using a novel DMAP catalyst

We describe the first catalytic dynamic kinetic resolution of hemiaminals mediated by an organocatalyst. A 0.1-1 mol % catalyst loading is effective for the dynamic kinetic resolution of hemiaminals to produce esters up to 88% ee in high yields. A 10 mol % catalyst loading resulted in a decreased selectivity, whereas the selectivity increased at 50 °C. The absolute configuration is assigned on the basis of the empirical Cotton effect rule.