sodium hydroxide in water

1: With L-(+)-tartaric acid 2: With potassium carbonate

(2S,3S)-2,3-dihydroxybutanedioic acid

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

1: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C 2: rac. camphersulfonic acid / 15 h / Heating 3: H2; AcOH / Pd/C / ethanol / 3 h 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 6.1: H2; AcOH / Pd/C / ethanol / 3 h View Scheme

1: rac. camphersulfonic acid / 15 h / Heating 2: H2; AcOH / Pd/C / ethanol / 3 h 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 5.1: H2; AcOH / Pd/C / ethanol / 3 h 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 4: H2; AcOH / Pd/C / ethanol / 3 h View Scheme

1: Raney nickel; dioxane / 165 °C / 110326 - 220652 Torr / Hydrogenation 2: Dg-tartaric acid View Scheme