Fig. 7: Synthetic transformations of axially chiral N-indolylquinolinones. | Nature Communications

Fig. 7: Synthetic transformations of axially chiral N-indolylquinolinones.

From: Stereospecific positional alkene isomerization enables bidirectional central-to-axial chirality transfer

Fig. 7

All the reactions were performed at 0.1 mmol scale. a MeI (0.15 mmol), NaH (0.1 mmol), THF (1.0 mL), 0 °C to rt, 12 h. b Me3O+BF4- (0.15 mmol), DCM (1.0 mL), rt for 4 h. c H2SO4 aq. (6 N, 1.0 mL), MeOH (1.0 mL), 110 °C for 24 h. d NaOH aq. (4N, 1.0 mL), MeOH (1.0 mL), 40 °C for 6 h. e Diisobutylaluminium hydride (DIBAL-H, 1 M in THF, 0.2 mmol), THF, 0 °C for 18 h. f Raney Ni (30 mg), H2 ballon, MeOH (1.0 mL), 50 °C for 8 h. g NaN3 (0.4 mmol), NH4Cl (0.1 mmol), DMF (1.0 mL), 120 °C for 12 h. h (S)-tert-leucinol (0.15 mmol), ZnCl2 (0.1 mmol), chlorobenzene (1.0 mL), 140 °C for 18 h.

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