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Abstract A new racemic naphthyl‐coumarin‐based probe was found to bind covalently with amino acids in MeOH‐KOH system and thereby generates distinct CD responses. The induced strong CD signals allowed quantitative enantiomeric excess analysis of amino acids and enantioselective sensing of amines and amino alcohols. The mechanism for the reaction of the coumarin‐aldehyde probe with an amino acid was investigated by CD, UV‐Vis, NMR, ESI‐MS analyses and ECD calculation.