We herein report an opera:onally simple protocol for the installa:on of a free NH2-group in the a-posi:on of different carbonyl compounds by using aqueous ammonia as the nitrogensource. Key to success is a carefully op:mized phase-transfer catalysis approach using hypochlorites (i.e. Ca(OCl)2) in combina:on with quaternary ammonium salt catalysts which allows for the efficient direct a-amina:on of cyclic b-ketoesters, oxindoles and acyclic esters. Control experiments performed in the presence of radical traps like BHT (ditertbutylhydroxytoluene), PBN (N-tert-butyl-a-phenylnitrone), or DPE (1,1-diphenylethene) showed that these addi:ves have no effect, thus ruling out a mechanis:c scenario involving radical intermediates. Thus, we currently assume that these reac:ons proceed via in situ forma:on of monochloramine (NH2Cl), 21 which then serves as an electrophilic NH2-transfer agent. We also succeeded in obtaining a first proof-of-concept for an asymmetric protocol which, despite being far from perfect, in our opinion represents a promising basis for further catalyst varia:ons and development.