in tetrahydrofuran Product distribution / selectivity;

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: tetrahydrofuran / -10 °C / Inert atmosphere 2.2: 15 - 30 °C / Cooling View Scheme

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 1.2: 1.5 h / 25 °C / Inert atmosphere 1.3: pH 5 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 8 h / 25 °C / Inert atmosphere 3.1: water / 24 h / 25 °C 4.1: sodium iodide; cerium(III) chloride heptahydrate / acetonitrile / 2 h / 80 - 85 °C View Scheme

1.1: diisobutylaluminium hydride / toluene / 1 h / -65 - -60 °C / Inert atmosphere 1.2: 1 h / 25 °C / Inert atmosphere 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 2.2: 1.5 h / 25 °C / Inert atmosphere 2.3: pH 5 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 8 h / 25 °C / Inert atmosphere 4.1: water / 24 h / 25 °C 5.1: sodium iodide; cerium(III) chloride heptahydrate / acetonitrile / 2 h / 80 - 85 °C View Scheme

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 8 h / 25 °C / Inert atmosphere 2: water / 24 h / 25 °C 3: sodium iodide; cerium(III) chloride heptahydrate / acetonitrile / 2 h / 80 - 85 °C View Scheme

1: water / 24 h / 25 °C 2: sodium iodide; cerium(III) chloride heptahydrate / acetonitrile / 2 h / 80 - 85 °C View Scheme

1.1: potassium carbonate; methanol / dichloromethane / 25 - 30 °C 1.2: pH 4 2.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 6 h / -80 - -76 °C 2.2: -80 - -76 °C 3.1: potassium tert-butylate / tetrahydrofuran / -12 - 10 °C 3.2: 12 h / 25 - 30 °C 3.3: 48 h / 25 - 30 °C View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 0 °C 2.1: B-chloro-diisopinocampheylborane / n-heptane; tetrahydrofuran / 5 h / -30 - -25 °C / Inert atmosphere 2.2: 10 h / 20 °C 3.1: 1H-imidazole / dichloromethane / 18 h / 20 °C 4.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -30 °C / Inert atmosphere 4.2: -30 °C 5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 5.2: 3.25 h / 0 - 20 °C 6.1: potassium carbonate / acetone / 18 h / 20 °C 7.1: water / tetrahydrofuran / 52 h / 20 °C 8.1: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C 8.2: pH 6.8 / Aqueous phosphate buffer View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 0 °C 2.1: B-chloro-diisopinocampheylborane / n-heptane; tetrahydrofuran / 5 h / -30 - -25 °C / Inert atmosphere 2.2: 10 h / 20 °C 3.1: 1H-imidazole / dichloromethane / 18 h / 20 °C 4.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -30 °C / Inert atmosphere 4.2: -30 °C 5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 5.2: 3.25 h / 0 - 20 °C 6.1: potassium carbonate / acetone / 18 h / 20 °C 7.1: water / tetrahydrofuran / 52 h / 20 °C 8.1: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C 8.2: pH 6.8 / Aqueous phosphate buffer View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 3.25 h / 0 - 20 °C 2.1: potassium carbonate / acetone / 18 h / 20 °C 3.1: water / tetrahydrofuran / 52 h / 20 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C 4.2: pH 6.8 / Aqueous phosphate buffer View Scheme