diphenyl-phosphinic acid; sodium hydrogencarbonate in N,N-dimethyl-formamide T=4°C; 24 h;

diphenyl phosphoryl azide; sodium hydrogencarbonate in N,N-dimethyl-formamide T=0°C; 24 h; Inert atmosphere;

DMDO in dichloromethane T=-78 - -50°C; 1 h;

1: 71 percent / PMe3; H2O / tetrahydrofuran; toluene / 2 h / 25 °C 2: 43 percent / DPPA; NaHCO3 / dimethylformamide / 24 h / 4 °C View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 1.2: 1 h / 45 °C 2.1: triphenylphosphine / tetrahydrofuran / 14 h / 45 °C / Inert atmosphere 2.2: 4 h / 45 °C 3.1: sodium hydrogencarbonate; diphenyl phosphoryl azide / N,N-dimethyl-formamide / 24 h / 0 - 4 °C / Inert atmosphere View Scheme

1: tetrahydrofuran / 1 h / 25 °C 2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 3: tetrahydrofuran / 19 h / 40 °C 4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 6: 82 percent / p-TsOH / acetone / 22 h / 20 °C 7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 8: TFA / CH2Cl2 / 2 h / 20 °C 9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme

1: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C 2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 3: tetrahydrofuran / 19 h / 40 °C 4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 6: 82 percent / p-TsOH / acetone / 22 h / 20 °C 7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 8: TFA / CH2Cl2 / 2 h / 20 °C 9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme

1: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 2: tetrahydrofuran / 19 h / 40 °C 3: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 4: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 5: 82 percent / p-TsOH / acetone / 22 h / 20 °C 6: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 7: TFA / CH2Cl2 / 2 h / 20 °C 8: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 9: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 10: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme

1: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 2: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme

1: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 2: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 3: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme