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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 3 ·Et 2 O-based fluorinations, have not yet been addressed. Here we report the catalytic asymmetric nucleophilic fluorination using BF 3 ·Et 2 O as the fluorine reagent in the presence of chiral iodine catalyst. Various chiral fluorinated oxazine products were obtained with good to excellent enantioselectivities (up to >99% ee) and diastereoselectivities (up to >20:1 dr). Control experiments (the desired fluoro-oxazines could not be obtained when Py·HF or Et 3 N·3HF were employed as the fluorine source) indicated that BF 3 ·Et 2 O acted not only as a fluorine reagent but also as the activating reagent for activation of iodosylbenzene.

Catalytic asymmetric nucleophilic fluorination using BF3·Et2O as fluorine source and activating reagent