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The effect of the electronic nature of the para substituent on the aromatic ring of 2‐aryloxypropionyl chlorides on the stereochemical outcome of the acylation of 3,4‐dihydro‐3‐methyl‐2H‐[1,4]benzoxazine and its 7,8‐difluoro‐containing analogue has been studied. The geometries of the diastereoisomeric transition states and the corresponding Gibbs free enthalpies of activation were determined through DFT calculations at the COSMO‐CH2Cl2‐B3LYP‐D3‐gCP/def2‐TZVP (or def2‐SVP)//B3LYP‐D3‐gCP/def2‐SVP level of theory. It has been found that a low‐cost quantum chemical calculation at a chosen level of theory describes well the quantitative dependence of the selectivity of acylation on the structures of the reagents. The obtained results indicate that aromatic interactions between the reagents play a significant role in the process of stereodifferentiation, ensuring high selectivity of the acylation of benzoxazines with 2‐aryloxyacyl chlorides.

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