2-chloro-1-methyl-pyridinium iodide; triethylamine in dichloromethane T=20°C; Mukaiyama reaction; 48 h; Inert atmosphere;

1: 61 percent / Et3N; DMAP 2: 80 percent / PCC / CH2Cl2 3: MgSO4 / CH2Cl2 4: CuI; BF3*Et2O / tetrahydrofuran / -65 - -30 °C 5: HCO2NH4; Pd/C / methanol / Heating 6: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane 7: TBAF / tetrahydrofuran / 0 °C 8: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 9: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane 2: TBAF / tetrahydrofuran / 0 °C 3: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 4: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: 80 percent / PCC / CH2Cl2 2: MgSO4 / CH2Cl2 3: CuI; BF3*Et2O / tetrahydrofuran / -65 - -30 °C 4: HCO2NH4; Pd/C / methanol / Heating 5: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane 6: TBAF / tetrahydrofuran / 0 °C 7: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 8: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: MgSO4 / CH2Cl2 2: CuI; BF3*Et2O / tetrahydrofuran / -65 - -30 °C 3: HCO2NH4; Pd/C / methanol / Heating 4: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane 5: TBAF / tetrahydrofuran / 0 °C 6: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 7: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 2: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane 2: TBAF / tetrahydrofuran / 0 °C 3: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 4: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: CuI; BF3*Et2O / tetrahydrofuran / -65 - -30 °C 2: HCO2NH4; Pd/C / methanol / Heating 3: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane 4: TBAF / tetrahydrofuran / 0 °C 5: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 6: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: TBAF / tetrahydrofuran / 0 °C 2: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 3: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: HCO2NH4; Pd/C / methanol / Heating 2: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane 3: TBAF / tetrahydrofuran / 0 °C 4: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 5: TBTU; DIEA / dimethylformamide / 20 °C View Scheme