1: With diisobutylaluminium hydride in diethyl ether T=-78 - -65°C; 0.583333 h; 2: With water in diethyl ether

1: With lithium tri-t-butoxyaluminum hydride in diethyl ether T=20°C; 2 h; 2: With potassium hydrogensulfate in diethyl ether; water

1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 0.17 h / 0 °C 2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 42 h / 20 °C 3: lithium tri-t-butoxyaluminum hydride / diethyl ether / 2 h / 20 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 42 h / 20 °C 2: lithium tri-t-butoxyaluminum hydride / diethyl ether / 2 h / 20 °C View Scheme

1.1: dichloromethane; hexane; methanol / 1 h / 0 °C 1.2: 24 h / 20 °C 2.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.58 h / -78 - -65 °C 2.2: 0.5 h / -65 - 20 °C View Scheme

1.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 2.2: 6 h / 20 - 35 °C 3.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr 4.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h View Scheme

1.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 2.2: 6 h / 20 - 35 °C 3.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr 4.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 5.2: 2.5 h / -35 °C 6.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1: With N,N,N',N'-tetramethylguanidine in toluene T=0°C; 0.5 h; 2: With methanesulfonyl chloride; triethylamine in toluene T=0 - 20°C; 1.5 h; Alkaline aqueous solution;

1: benzyl N,N-di-Boc-D-glutamate-γ-semialdehyde; nitromethane With N,N,N',N'-tetramethylguanidine in toluene T=0°C; 0.5 h; 2: methanesulfonyl chloride With triethylamine in toluene T=0 - 20°C; 1.5 h;

1.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 2.2: 6 h / 20 - 35 °C 3.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr View Scheme