Quinoline → 5-(4-fluorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline

Participants

Reaction Steps

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and 4-fluorobenzaldehyde (0.093 g, 80 μL, 0.75 mmol) with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (0.179 g, 146 μL, 0.60 mmol) in the presence of KF (0.070 g, 1.2 mmol) and 18-crown-6 (0.317 g, 1.2 mmol) in THF (2.0 mL) at 10° C. to room temperature for 12 hrs followed by flash column chromatography (Pet. ether/EtOAc=75/25) of the crude reaction mixture afforded 5-(4-fluorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as inseparable mixture of diastereomers as a yellow solid (0.158 g, 96% yield, dr determined by 1H NMR analysis of crude reaction mixture is >20:1).

Provenance & Evidence