1: 2,6-lutidine 2: I2; CF3CO2Ag / CHCl3 3: Et2NH; CuI / (Ph3P)2PdCl2 / dimethylsulfoxide 4: TBAF / tetrahydrofuran 5: (COCl)2; DMSO; Et3N 7: (COCl)2; DMSO; Et3N 9: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 10: Ph3P; H2O 11: Et3N 12: 70 percent / 1,2-dichloro-benzene / Heating 13: LiOH 15: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 16: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 17: HCl View Scheme

1.1: 98 percent / 2,6-lutidine / CH2Cl2 / 5 h / 20 °C 2.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C 3.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C 4.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C 5.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 6.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C 6.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 6.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 7.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 8.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 9.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 10.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 11.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 12.1: 60 percent / various solvent(s) / 66 h / Heating 13.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 14.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 15.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 16.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 17.1: HCl / diethyl ether / 1 h / 20 °C 17.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

1: With lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 4 h; Inert atmosphereReflux; 2: With water; sodium sulfate in tetrahydrofuran; diethyl ether

1: 81 percent / H2SO4 / Heating 2: 100 percent / DIBAL-H / CH2Cl2; toluene / 1.5 h / -78 °C 3: 86 percent / Ni(OAc)2*4H2O; NaBH4; H2 / aq. ethanol View Scheme

borane-THF in tetrahydrofuran T=0 - 20°C;

lithium aluminium tetrahydride in tetrahydrofuran T=0 - 20°C;

in tetrahydrofuran

sodium tetrahydroborate; hydrogen; nickel diacetate in ethanol

lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 2.5 h; Reflux;

1: 100 percent / DIBAL-H / CH2Cl2; toluene / 1.5 h / -78 °C 2: 86 percent / Ni(OAc)2*4H2O; NaBH4; H2 / aq. ethanol View Scheme