We started our inves:ga:ons by tes:ng the a-amina:on of the cyclic b-ketoester 1a (Table gives a condensed overview of the most significant results obtained in a detailed screening of different reagents and condi:ons 17 ). Inspired by recent developments when using Quatsalts containing an easily oxidizable counter anion (i.e. I -or Br -which can in situ form cataly:cally competent higher oxida:on state species like IO -or Br3 -under oxida:ve condi:ons) we used Bu4NI as a catalyst first. We were soon able to iden:fy Ca(OCl)2 as a well-suited oxidant to achieve the forma:on of the targeted NH2-func:onalized 2a by reac:ng 1a with 4 eq. of aqueous ammonia (entries 1-4). Noteworthy, conversion of 1a was high in most of the ini:ally tested solvents, 17 but the reac:ons were accompanied by the forma:on of uniden:fied sideproducts as well as the corresponding a-chlorinated ketoester 3a and promising yields of >50% 2a were only achieved when aroma:c or chlorinated solvents were used (entries 1 and 4). We immediately tested if 3a may be an intermediate in the forma:on of 2a by reac:ng 3a with NH3 in the presence of Bu4NI, but no forma:on of 2a was observed hereby, thus ruling out an a-chlorina:on -nucleophilic subs:tu:on reac:on sequence.