Abstract　The　recognition　and　analysis　of　mono-functionalized　organics　is　an　intensive　area　of　research　in　organic　chemistry.　Toward　this　end,　an　in　situ-generated　metal-templated　dynamic　multi-component　covalent　assembly　for　the　reversible　binding　and　chirality　sensing　of　mono　secondary　amines　is　presented.　The　reaction　of　pyridine-2-carboxyaldhyde,　di(2-picolyl)amine,　zinc　triflate,　tetrabutylammonium　chloride,　and　a　series　of　secondary　amines,　affords　tripodal　aminal　zinc　complexes.　The　dynamic　nature　of　the　system　was　demonstrated　by　component　exchange　of　both　amines　and　aldehydes.　The　equilibrium　can　be　modulated　by　changing　counteranions,　concentrations,　as　well　as　structural　feature　of　the　amines.　The　competition　between　two　iminium　pathways　resulted　in　a　unique　distribution　of　components.　Due　to　the　enantiotopicity　of　iminiums,　decent　diastereoselectivity　was　observed　for　chiral　secondary　amines.　The　resulting　diastereomeric　helical　complexes　were　employed　for　the　determination　of　enantiomeric　excess　with　high　accuracy.　©　2015　Elsevier　Ltd.　All　rights　reserved.