2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; NaH2PO4 buffer; sodium hypochlorite in water; acetonitrile T=45°C; pH=6.6; 24 h;

lithium hydroxide in methanol T=20°C; 18 h;

1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h 2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 4.1: 78 percent / TEA; DMAP / CH2Cl2 5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 6.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 6.2: 70 percent / tetrahydrofuran / 20 °C 7.1: 81 percent / TBAF / tetrahydrofuran / 6 h / 20 °C 8.1: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 9.1: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

1.1: 78 percent / TEA; DMAP / CH2Cl2 2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 3.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 3.2: 70 percent / tetrahydrofuran / 20 °C 4.1: 81 percent / TBAF / tetrahydrofuran / 6 h / 20 °C 5.1: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 6.1: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

1.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 2.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 3.1: 78 percent / TEA; DMAP / CH2Cl2 4.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 5.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 5.2: 70 percent / tetrahydrofuran / 20 °C 6.1: 81 percent / TBAF / tetrahydrofuran / 6 h / 20 °C 7.1: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 8.1: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

1.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 2.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 2.2: 70 percent / tetrahydrofuran / 20 °C 3.1: 81 percent / TBAF / tetrahydrofuran / 6 h / 20 °C 4.1: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 5.1: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h 2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 4.1: 78 percent / TEA; DMAP / CH2Cl2 5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 6.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 6.2: 70 percent / tetrahydrofuran / 20 °C 7.1: 81 percent / TBAF / tetrahydrofuran / 6 h / 20 °C 8.1: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 9.1: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

1.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 1.2: 70 percent / tetrahydrofuran / 20 °C 2.1: 81 percent / TBAF / tetrahydrofuran / 6 h / 20 °C 3.1: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 4.1: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

1: 81 percent / TBAF / tetrahydrofuran / 6 h / 20 °C 2: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 3: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

1: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 2: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme