Catalytic asymmetric nucleophilic fluorination using BF·EtO as fluorine source and activating reagent.

Fluorination using chiral catalytic methods could result in a direct access to asymmetric fluorine chemistry. However, challenges in catalytic asymmetric fluorinations, especially the longstanding stereochemical challenges existed in BF·EtO-based fluorinations, have not yet been addressed. Here we report the catalytic asymmetric nucleophilic fluorination using BF·EtO as the fluorine reagent in the presence of chiral iodine catalyst.

Highly efficient regio-selective ring-opening nucleophilic fluorination of aziridines and azetidines: access to β- or γ-fluorinated amino acid derivatives.

Herein, we have presented a facile and efficient method of ring-opening nucleophilic fluorination of aziridines, affording highly regio-selective β-fluorinated amines. Firstly, the example of ring-opening hydrofluorination of azetidines was reported. Then, the Olah's reagent also provided a promising method for the construction of enantioenriched β-fluoro-α-amino acid derivatives, which could be used for the preparation of peptide-based bioactive molecules.