A fluorination-induced intramolecular cyclization for the synthesis of fluoro-substituted spiro-1,3-oxazine and spiro-1,3-thiazine derivatives is described. N-(2-(Cyclohex-1-en-1-yl)ethyl)benzamide and benzothioamide are used as the substrates, and the cationic fluorinating agent Selectfluor works as the fluoride source. The reaction yields a single diastereomer. The scope of this regioselective fluorination reaction is established by preparing thirty different spirooxazine and spirothiazine derivatives.