Synthesis and Evaluation of Two Coumarin‐Type Derivatization Reagents for Fluorescence Detection of Chiral Amines and Chiral Carboxylic Acids

The synthesis of two fluorescent coumarin‐type chiral derivatization agents ( 4 and 11 ) is reported. A chiral side chain was introduced at position 7 of the coumarin via Mitsunobu reaction. The two coumarins bear in this side chain either a free amino group or a carboxyl group, making them useful for further transformations. Conjugates of chiral prototype drugs with 4 or 11 were prepared by amide coupling of the analyte's carboxyl group to the reagent's amine group, or vice versa. The separation of seven diastereomeric conjugates through achiral high‐performance liquid chromatography (HPLC) on a common C18 column is demonstrated. Chirality 25:957–964, 2013. © 2013 Wiley Periodicals, Inc.