1.1: tert.-butyl lithium / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere 1.2: 3.58 h / 0 °C / Inert atmosphere; Reflux 2.1: toluene-4-sulfonic acid / tetrahydrofuran / 2 h / Inert atmosphere; Reflux 3.1: tributylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 4 - 25 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium carbonate / toluene / 16 h / 110 °C / Inert atmosphere 4.2: 16 h / 0 - 25 °C / Inert atmosphere 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / N,N-dimethyl-formamide / 16 h / 0 - 25 °C / Inert atmosphere 6.1: trifluoroacetic acid / dichloromethane / 1 h / Inert atmosphere 7.1: water / acetonitrile / Inert atmosphere; Acidic conditions View Scheme

hydrogen bromide; acetic acid

暂无反应条件数据

1: 80 percent / NaH / dimethylformamide / 18 h / 25 °C 2: 86 percent / 5 N NaOH / benzene / 12 h / 25 °C 3: 1.) (Sia)2BH, 2.) H2O2, NaOH / 1.) THF, 0 deg C, 1 h, 2.) THF, 0 deg C, 1 h 4: 93 percent / TsOH / methanol / 4 h / 25 °C 5: 92 percent / CBr4, (C6H5)3P / acetonitrile / 1 h / 25 °C View Scheme

sodium hydroxide; copper(II) sulfate 5 h; Heating;

1.1: [(ν3-C3H5)PdCl]2; (1S,2S)-bis(N,N'-(o-(PPh2)C6H4CO)-1,2-diphenylethylamine; Et3N / CH2Cl2 / 8 h / 20 °C 2.1: TsOH*H2O / methanol / 4 h / 50 °C 3.1: DIBAlH / toluene; hexane / 1.5 h / -78 °C 4.1: Ph3P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C 4.2: diethyl ether / 12 h / -20 - 20 °C 4.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C 5.1: 91 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C 6.1: 91 percent / PPh3 / CH2Cl2 / 0.17 h / 0 °C 7.1: 88 percent / Pd(PPh3)4; Bu3SnH / toluene / 0.33 h 8.1: 65 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C 9.1: SeO2; quartz sand / dioxane / 1.33 h / 75 °C 10.1: DIBALH / CH2Cl2; hexane; diethyl ether / -78 - 0 °C 10.2: NH4Br / various solvents / 2 h / 20 °C 10.3: 89 percent / NaBH4 / various solvents / 20 °C 11.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C 11.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation 12.1: BBr3 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: [(ν3-C3H5)PdCl]2; (1S,2S)-bis(N,N'-(o-(PPh2)C6H4CO)-1,2-diphenylethylamine; Et3N / CH2Cl2 / 8 h / 20 °C 2.1: TsOH*H2O / methanol / 4 h / 50 °C 3.1: DIBAlH / toluene; hexane / 1.5 h / -78 °C 4.1: Ph3P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C 4.2: diethyl ether / 12 h / -20 - 20 °C 4.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C 5.1: 91 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C 6.1: 91 percent / PPh3 / CH2Cl2 / 0.17 h / 0 °C 7.1: 88 percent / Pd(PPh3)4; Bu3SnH / toluene / 0.33 h 8.1: 65 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C 9.1: SeO2; quartz sand / dioxane / 1.33 h / 75 °C 10.1: DIBALH / CH2Cl2; hexane; diethyl ether / -78 - 0 °C 10.2: NH4Br / various solvents / 2 h / 20 °C 10.3: 89 percent / NaBH4 / various solvents / 20 °C 11.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C 11.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation View Scheme

1: 96 percent / KOH / H2O / 15 h / 50 °C 3: 94 percent / NaBH4 / ethanol / 1.)2 h, 0-5 deg C, 2.) 12 h, 25 deg C View Scheme

1: AlCl3, Py 2: NaH 3: (i) LiAlH4, (ii) MnO2 View Scheme