1: With ammonium cerium (IV) nitrate in acetonitrile T=20°C; 0.166667 h; 2: With sodium hydroxide in acetonitrile 6 h; 3: With hydrogenchloride in water; acetonitrile optical yield given as percent ee;

1.1: sodium hydroxide / methanol; water / 2 h / 20 °C 2.1: 4-(N,N-dimethlyamino)pyridine; BOP; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 3.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 0 - 20 °C 4.1: pyridine; phosphorus pentachloride / dichloromethane / 8 h / 0 °C 5.1: dichloromethane / 1 h / -30 - -20 °C 6.1: water / dichloromethane / 12 h / 20 °C 7.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 8.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 8.2: 2 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 10.1: pyridine; 4-(N,N-dimethlyamino)pyridine; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 10.2: 0.25 h / 20 °C View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; BOP; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 0 - 20 °C 3.1: pyridine; phosphorus pentachloride / dichloromethane / 8 h / 0 °C 4.1: dichloromethane / 1 h / -30 - -20 °C 5.1: water / dichloromethane / 12 h / 20 °C 6.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 7.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 7.2: 2 h / 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 9.1: pyridine; 4-(N,N-dimethlyamino)pyridine; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 9.2: 0.25 h / 20 °C View Scheme

1.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 0 - 20 °C 2.1: pyridine; phosphorus pentachloride / dichloromethane / 8 h / 0 °C 3.1: dichloromethane / 1 h / -30 - -20 °C 4.1: water / dichloromethane / 12 h / 20 °C 5.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 6.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 8.1: pyridine; 4-(N,N-dimethlyamino)pyridine; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 8.2: 0.25 h / 20 °C View Scheme

1.1: pyridine; phosphorus pentachloride / dichloromethane / 8 h / 0 °C 2.1: dichloromethane / 1 h / -30 - -20 °C 3.1: water / dichloromethane / 12 h / 20 °C 4.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 5.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 7.1: pyridine; 4-(N,N-dimethlyamino)pyridine; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 7.2: 0.25 h / 20 °C View Scheme

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 2.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 2.2: 2 h / 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4.1: pyridine; 4-(N,N-dimethlyamino)pyridine; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 4.2: 0.25 h / 20 °C View Scheme

1.1: C20H24N2O2 / tetrahydrofuran / 1 h / 30 °C 1.2: 1 h / 25 °C 1.3: 10 h / 100 °C 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.33 h / 20 °C 2.2: 0.25 h / 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine; zinc / 2 h / 20 °C 4.1: ammonium cerium (IV) nitrate / acetonitrile / 0.17 h / 20 °C 4.2: 6 h View Scheme

sodium hydroxide in methanol

1.1: tris(triphenylphosphine)ruthenium(II) chloride; C48H50N2O2P2Ru; potassium tert-butylate; hydrogen / isopropyl alcohol / 24 h / 0 °C / 7600.51 Torr / Reflux; Autoclave 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.33 h / 20 °C 2.2: 0.25 h / 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine; zinc / 2 h / 20 °C 4.1: ammonium cerium (IV) nitrate / acetonitrile / 0.17 h / 20 °C 4.2: 6 h View Scheme

1.1: Dess-Martin periodane / 0.25 h / 0 °C 2.1: tris(triphenylphosphine)ruthenium(II) chloride; C48H50N2O2P2Ru; potassium tert-butylate; hydrogen / isopropyl alcohol / 24 h / 0 °C / 7600.51 Torr / Reflux; Autoclave 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.33 h / 20 °C 3.2: 0.25 h / 20 °C 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine; zinc / 2 h / 20 °C 5.1: ammonium cerium (IV) nitrate / acetonitrile / 0.17 h / 20 °C 5.2: 6 h View Scheme