Beschreibung:
<jats:title>Abstract</jats:title><jats:p>A one‐pot enantioselective route to <jats:italic>N</jats:italic>‐unprotected 2,3‐dihydro‐1,5‐benzothiazepinones, by an organocatalyzed sulfa‐Michael reaction of readily available α,β‐unsaturated <jats:italic>N</jats:italic>‐acyl pyrazoles with 2‐aminothiophenols followed by silica‐gel‐catalyzed lactamization, has been developed. The method proceeds under mild conditions at room temperature and it requires only 1 mol % catalyst loading, to give 2‐aryl/alkyl‐substituted 1,5‐benzothiazepines in generally good to excellent yields and enantioselectivities. The process, used for a short synthesis of antidepressant drug (<jats:italic>R</jats:italic>)‐(−)‐thiazesim, represents the first method to access enantioenriched unprotected 1,5‐benzothiazepines, which are useful for rapid derivatization in drug discovery.</jats:p>