hydrogen; ethylenediamine in ethanol; water stereoselective reaction;

sulfuric acid T=20°C;

1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C 1.2: -20 - 20 °C 2.1: Jone's reagent / acetone / 0 - 4 °C 3.1: sulfuric acid / 20 °C View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C 2.2: -20 - 20 °C 3.1: Jone's reagent / acetone / 0 - 4 °C 4.1: sulfuric acid / 20 °C View Scheme

1: Jone's reagent / acetone / 0 - 4 °C 2: sulfuric acid / 20 °C View Scheme

1: hydrogen; ethylenediamine / ethanol; water 2: 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine / dimethyl sulfoxide / 20 °C View Scheme