In conclusion, we have developed a practically simple and sustainable process for the site-selective carbanion generation from C(sp 3 )-H bonds in the α-amine position. Applying this methodology, numerous amines have been selectively deuterated/tritiated with a high degree of regioselectivity. In addition, the methodology was further extended to the synthesis of various 1,2-amino alcohols, including drug molecules. The practical utility of this method was further demonstrated by conducting bulk scale reactions. Based on several mechanistic experiments, including spectroscopic analysis, we propose a possible reaction pathway and offer a rational for the observed selectivity.