Kinetic Resolution of Thioformamides

Significance

The authors present a unique approach to the catalytic kinetic resolution of amine derivatives based on formamide and thioform­amide substrates using peptide 1 as the catalyst. High enantioselectivities (er from 79:21 to 97.5:2.5) and selectivity factors (up to 43.7) were achieved utilizing Boc₂O as the reagent at room temperature. Formamides can also undergo kinetic resolution under the same conditions, but their thioform­amide analogues showed better reactivity and higher selectivity. Transformation of the Boc-protected thioformamide products to other practical amine derivatives, such as N-Boc amines and the parent formamide compounds, was also demonstrated.