hydrogen; [Rh((S,S,R,R)-Tangphos)NBD][SbF6] in dichloromethane T=80°C; P=77572.2 Torr; 72 h; Title compound not separated from byproducts;

1: 90 percent / H2 / 5 percent Pd-C / aq. ethanol / 36 h / 20 °C / 5171.48 Torr 2: BuLi / -78 °C 3: H2 / [Rh((S,S,R,R)-Tangphos)NBD][SbF6] / CH2Cl2 / 72 h / 80 °C / 77572.2 Torr View Scheme

1: BuLi / -78 °C 2: H2 / [Rh((S,S,R,R)-Tangphos)NBD][SbF6] / CH2Cl2 / 72 h / 80 °C / 77572.2 Torr View Scheme

1: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C 2: rac. camphersulfonic acid / 15 h / Heating View Scheme

1.1: BuLi / tetrahydrofuran / 0.17 h / -30 °C 1.2: 87 percent / tetrahydrofuran / 2 h / 0 °C 2.1: TiCl4; Et3N / CH2Cl2 / 0.5 h / -15 °C 2.2: TiCl4 / CH2Cl2 / 3 h / 0 °C 3.1: 80 percent / NaH; Bu4NI / dimethylformamide / 3 h / 70 °C 4.1: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C 5.1: rac. camphersulfonic acid / 15 h / Heating View Scheme

1.1: TiCl4; Et3N / CH2Cl2 / 0.5 h / -15 °C 1.2: TiCl4 / CH2Cl2 / 3 h / 0 °C 2.1: 80 percent / NaH; Bu4NI / dimethylformamide / 3 h / 70 °C 3.1: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C 4.1: rac. camphersulfonic acid / 15 h / Heating View Scheme

1: 80 percent / NaH; Bu4NI / dimethylformamide / 3 h / 70 °C 2: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C 3: rac. camphersulfonic acid / 15 h / Heating View Scheme

camphor-10-sulfonic acid 15 h; Heating;

hydrogen; acetic acid; palladium on activated charcoal in ethanol 3 h;