Fig. 3: Substrate scope of the nucleophilic asymmetric fluorinations. | Nature Communications

Fig. 3: Substrate scope of the nucleophilic asymmetric fluorinations.

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

Fig. 3

Reactions were conducted on a 0.2 mmol scale with 10.0 equivalents of BF3·Et2O in DCE (8.0 mL) at −25 °C for 48 h. The absolute configuration of 4b was assigned by X-ray crystallography (structure shown), and the configuration of all other products was assigned by analogy. a Substrate scope of N-cinnamylbenzamides bearing various substituents on Ar1 and Ar2 ring. b Substrate scope of N-cinnamylbenzamides with “complex substituents” on Ar2 ring and Ar2 = heterocyclic groups. c Gram-scale reaction with 4a, CIC1, m-CPBA and BF3·Et2O. Isolated yields are reported. *The ee values of 30b and 31b could not be detected by HPLC. †CIC2 was employed as the catalyst for 42b. The ee values were determined by chiral HPLC analysis and the dr values were determined by 19F NMR. t-Bu, tert-butyl; Ph, phenyl; Me, methyl; Ac, acetyl.

Back to article page