1: With sodium dithionite; sodium hydrogencarbonate in tetrahydrofuran; water 1.25 h; 2: With hydrogenchloride in methanol; ethyl acetate T=20 - 60°C; 0.0833333 h;

1: With C39H60N4O4; scandium tris(trifluoromethanesulfonate) in chloroform T=35°C; 0.5 h; Inert atmosphere; 2: With sodium carbonate; N-fluoro-N-(phenylsulfonyl)benzene-sulfonamide in chloroform T=0°C; 72 h; Inert atmosphere; enantioselective reaction;

trifluoroacetic acid in dichloromethane T=20°C; 8 h;

1.1: 78 percent / 4 h / 80 °C 2.1: s-BuLi / cyclohexane; hexane; tetrahydrofuran / 3 h / -40 °C 2.2: 87 percent / cyclohexane; hexane; tetrahydrofuran / 1 h / -78 °C 3.1: 96 percent / aq. HCl / tetrahydrofuran / 6 h / Heating 4.1: NaH / tetrahydrofuran / 1 h / 0 °C 4.2: 81 percent / tetrahydrofuran / 4 h / -20 - 20 °C 5.1: 76 percent / Et3SiH; TFA / 48 h / 110 - 120 °C 6.1: 80 percent / EtMgBr / tetrahydrofuran / 3 h / 20 °C 7.1: N-fluorobenzenesulfonimide; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-) / acetone / 18 h / 0 °C 8.1: TFA / CH2Cl2 / 8 h / 20 °C View Scheme

1.1: s-BuLi / cyclohexane; hexane; tetrahydrofuran / 3 h / -40 °C 1.2: 87 percent / cyclohexane; hexane; tetrahydrofuran / 1 h / -78 °C 2.1: 96 percent / aq. HCl / tetrahydrofuran / 6 h / Heating 3.1: NaH / tetrahydrofuran / 1 h / 0 °C 3.2: 81 percent / tetrahydrofuran / 4 h / -20 - 20 °C 4.1: 76 percent / Et3SiH; TFA / 48 h / 110 - 120 °C 5.1: 80 percent / EtMgBr / tetrahydrofuran / 3 h / 20 °C 6.1: N-fluorobenzenesulfonimide; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-) / acetone / 18 h / 0 °C 7.1: TFA / CH2Cl2 / 8 h / 20 °C View Scheme

1.1: 96 percent / aq. HCl / tetrahydrofuran / 6 h / Heating 2.1: NaH / tetrahydrofuran / 1 h / 0 °C 2.2: 81 percent / tetrahydrofuran / 4 h / -20 - 20 °C 3.1: 76 percent / Et3SiH; TFA / 48 h / 110 - 120 °C 4.1: 80 percent / EtMgBr / tetrahydrofuran / 3 h / 20 °C 5.1: N-fluorobenzenesulfonimide; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-) / acetone / 18 h / 0 °C 6.1: TFA / CH2Cl2 / 8 h / 20 °C View Scheme

1.1: LiHMDS / tetrahydrofuran / 1.5 h / -10 °C 1.2: N-fluoro-2-naphthoylquininium tetrafluoroborate / tetrahydrofuran; acetonitrile / -40 - 5 °C 2.1: Na2S2O4 2.2: HCl View Scheme

1.1: LiHMDS / tetrahydrofuran / 1.5 h / -10 °C 1.2: N-fluoro-2-naphthoylquininium tetrafluoroborate / tetrahydrofuran; acetonitrile / -40 - 5 °C 2.1: Na2S2O4 2.2: HCl View Scheme

NF-QD in dichloromethane T=-80°C; Title compound not separated from byproducts;

1.1: (S)-(-)-α-methylbenzylamine 1.2: NaOH 2.1: Na2S2O4 3.1: HCl View Scheme