1: 57 percent / SeO2; NaH2PO4 / dioxane / 3 h / 150 °C 2: methanol 3: diisobutylaluminum hydride 4: sodium cyanoborohydride / H2O View Scheme

1: 91 percent / Pd(OAc)2; bis(diphenylphosphanyl)propane; Ag2CO3 / toluene / 24 h / 107 °C 2: 57 percent / SeO2; NaH2PO4 / dioxane / 3 h / 150 °C 3: methanol 4: diisobutylaluminum hydride 5: sodium cyanoborohydride / H2O View Scheme

1: triphenylphosphine; diisopropyl azodicarboxylate / diethyl ether 2: p-toluenesolfonic acid; water / tetrahydrofuran 3: 91 percent / Pd(OAc)2; bis(diphenylphosphanyl)propane; Ag2CO3 / toluene / 24 h / 107 °C 4: 57 percent / SeO2; NaH2PO4 / dioxane / 3 h / 150 °C 5: methanol 6: diisobutylaluminum hydride 7: sodium cyanoborohydride / H2O View Scheme

1: p-toluenesolfonic acid; water / tetrahydrofuran 2: 91 percent / Pd(OAc)2; bis(diphenylphosphanyl)propane; Ag2CO3 / toluene / 24 h / 107 °C 3: 57 percent / SeO2; NaH2PO4 / dioxane / 3 h / 150 °C 4: methanol 5: diisobutylaluminum hydride 6: sodium cyanoborohydride / H2O View Scheme

1.1: TFA / CH2Cl2 / 20 °C 2.1: NaCNBH3; 4 Angstroem molecular sieves / methanol / 0 °C 3.1: TsOH / CH2Cl2 / 20 °C 3.2: dimethyldioxirane / CH2Cl2 / 20 °C 3.3: 45 percent / DBU / CH2Cl2 / 20 °C 4.1: 98 percent / NaBH4 / ethanol / 80 °C 5.1: NaIO4 / tetrahydrofuran; H2O / 20 °C 5.2: 64 percent / CH2Cl2 / 70 °C 6.1: 50 percent / Ph3SiOReO3; TsOH / benzene / 60 °C View Scheme

1.1: (1S,2S)-(1,2-bis[NHCO(o-Ph2P)phenyl]-1,2-diphenyl)ethane; [η3-C3H5PdCl]2; Et3N / CH2Cl2 / 8 h / 20 °C 2.1: 92 percent / DIBAL-H / toluene / -78 °C 3.1: 97 percent / 2,6-lutidine / CH2Cl2 / 20 °C 4.1: Pd(OAc)2; 1,2-bis(dicyclohexylphosphino)ethane / N,N-dimethyl-acetamide / 80 °C 4.2: TBAF / tetrahydrofuran / 20 °C 5.1: 97 percent / MnO2 / acetone / 20 °C 6.1: NaCNBH3 / methanol / Heating 7.1: Et3N / CH2Cl2 / 20 °C 8.1: 93 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C 9.1: NaN(TMS)2 / tetrahydrofuran / 0 °C 10.1: TFA / CH2Cl2 / 20 °C 11.1: NaCNBH3; 4 Angstroem molecular sieves / methanol / 0 °C 12.1: TsOH / CH2Cl2 / 20 °C 12.2: dimethyldioxirane / CH2Cl2 / 20 °C 12.3: 45 percent / DBU / CH2Cl2 / 20 °C 13.1: 98 percent / NaBH4 / ethanol / 80 °C 14.1: NaIO4 / tetrahydrofuran; H2O / 20 °C 14.2: 64 percent / CH2Cl2 / 70 °C 15.1: 50 percent / Ph3SiOReO3; TsOH / benzene / 60 °C View Scheme

1.1: (1S,2S)-(1,2-bis[NHCO(o-Ph2P)phenyl]-1,2-diphenyl)ethane; [η3-C3H5PdCl]2; Et3N / CH2Cl2 / 8 h / 20 °C 2.1: 92 percent / DIBAL-H / toluene / -78 °C 3.1: 97 percent / 2,6-lutidine / CH2Cl2 / 20 °C 4.1: Pd(OAc)2; 1,2-bis(dicyclohexylphosphino)ethane / N,N-dimethyl-acetamide / 80 °C 4.2: TBAF / tetrahydrofuran / 20 °C 5.1: 97 percent / MnO2 / acetone / 20 °C 6.1: NaCNBH3 / methanol / Heating 7.1: Et3N / CH2Cl2 / 20 °C 8.1: 93 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C 9.1: NaN(TMS)2 / tetrahydrofuran / 0 °C 10.1: TFA / CH2Cl2 / 20 °C 11.1: NaCNBH3; 4 Angstroem molecular sieves / methanol / 0 °C 12.1: TsOH / CH2Cl2 / 20 °C 12.2: dimethyldioxirane / CH2Cl2 / 20 °C 12.3: 45 percent / DBU / CH2Cl2 / 20 °C 13.1: 98 percent / NaBH4 / ethanol / 80 °C 14.1: NaIO4 / tetrahydrofuran; H2O / 20 °C 14.2: 64 percent / CH2Cl2 / 70 °C 15.1: 50 percent / Ph3SiOReO3; TsOH / benzene / 60 °C View Scheme

1.1: NaCNBH3 / methanol / Heating 2.1: Et3N / CH2Cl2 / 20 °C 3.1: 93 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C 4.1: NaN(TMS)2 / tetrahydrofuran / 0 °C 5.1: TFA / CH2Cl2 / 20 °C 6.1: NaCNBH3; 4 Angstroem molecular sieves / methanol / 0 °C 7.1: TsOH / CH2Cl2 / 20 °C 7.2: dimethyldioxirane / CH2Cl2 / 20 °C 7.3: 45 percent / DBU / CH2Cl2 / 20 °C 8.1: 98 percent / NaBH4 / ethanol / 80 °C 9.1: NaIO4 / tetrahydrofuran; H2O / 20 °C 9.2: 64 percent / CH2Cl2 / 70 °C 10.1: 50 percent / Ph3SiOReO3; TsOH / benzene / 60 °C View Scheme

1.1: 97 percent / MnO2 / acetone / 20 °C 2.1: NaCNBH3 / methanol / Heating 3.1: Et3N / CH2Cl2 / 20 °C 4.1: 93 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C 5.1: NaN(TMS)2 / tetrahydrofuran / 0 °C 6.1: TFA / CH2Cl2 / 20 °C 7.1: NaCNBH3; 4 Angstroem molecular sieves / methanol / 0 °C 8.1: TsOH / CH2Cl2 / 20 °C 8.2: dimethyldioxirane / CH2Cl2 / 20 °C 8.3: 45 percent / DBU / CH2Cl2 / 20 °C 9.1: 98 percent / NaBH4 / ethanol / 80 °C 10.1: NaIO4 / tetrahydrofuran; H2O / 20 °C 10.2: 64 percent / CH2Cl2 / 70 °C 11.1: 50 percent / Ph3SiOReO3; TsOH / benzene / 60 °C View Scheme

1.1: Et3N / CH2Cl2 / 20 °C 2.1: 93 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C 3.1: NaN(TMS)2 / tetrahydrofuran / 0 °C 4.1: TFA / CH2Cl2 / 20 °C 5.1: NaCNBH3; 4 Angstroem molecular sieves / methanol / 0 °C 6.1: TsOH / CH2Cl2 / 20 °C 6.2: dimethyldioxirane / CH2Cl2 / 20 °C 6.3: 45 percent / DBU / CH2Cl2 / 20 °C 7.1: 98 percent / NaBH4 / ethanol / 80 °C 8.1: NaIO4 / tetrahydrofuran; H2O / 20 °C 8.2: 64 percent / CH2Cl2 / 70 °C 9.1: 50 percent / Ph3SiOReO3; TsOH / benzene / 60 °C View Scheme