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: 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 3.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 3.2: 1.5 h / 0 - 20 °C View Scheme

1.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.58 h / -78 - -65 °C 1.2: 0.5 h / -65 - 20 °C 2.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 2.2: 1.5 h / 0 - 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 3.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 3.2: 1.5 h / 0 - 20 °C View Scheme

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

1.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 1.2: 6 h / 20 - 35 °C 2.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr 3.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 4.2: 2.5 h / -35 °C 5.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 1.2: 6 h / 20 - 35 °C 2.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr View Scheme

water; sodium carbonate; [Ir(acetylacetonate)(1,5-cyclooctadiene)]; (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl in 1,4-dioxane T=20 - 35°C; 6 h; Alkaline aqueous solution;

Rh(acac)2(C2H4)2; sodium hydrogencarbonate; (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl in water T=35°C; Hayashi-Miyaura reaction; Inert atmosphere; Reactivity; TemperatureConcentrationReagent/catalyst; optical yield given as percent dediastereoselective reaction;