Highly enantioenriched 2,2-diarylethanols can be efficiently synthesized using the AgOTf-promoted Friedel–Crafts alkylation of (hetero)arenes with configurationally labile α-bromoarylacetates.

2-Aminophenol displays a diverse pattern of reactivity in the substitution reaction of α-bromoacetate. The substitution under neutral or basic conditions results in the formation of 1,4-benzoxazinones, whereas Lewis acid-promoted substitution leads to Friedel-Crafts alkylation of 2-aminophenol. Asymmetric synthesis of two regioisomeric 1,4-benzoxazinones is accomplished from the nucleophilic substitution of highly diastereoenriched α-aryl-α-bromoacetates with N-alkyl-2-aminophenols under varied reaction conditions.

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