1.1: n-BuLi; N,N'-dimethylpropyleneurea / hexane; tetrahydrofuran / 0.33 h / 0 °C 1.2: 92 percent / hexane; tetrahydrofuran / 0.5 h / 0 °C 2.1: diisobutylaluminum hydride / hexane; CH2Cl2 / 0.25 h / 0 °C 2.2: 82 percent / SiO2-H2O / hexane; CH2Cl2 View Scheme

1.1: n-BuLi; N,N'-dimethylpropyleneurea / hexane; tetrahydrofuran / 0.33 h / 0 °C 1.2: 92 percent / hexane; tetrahydrofuran / 0.5 h / 0 °C 2.1: diisobutylaluminum hydride / hexane; CH2Cl2 / 0.25 h / 0 °C 2.2: 82 percent / SiO2-H2O / hexane; CH2Cl2 View Scheme

1.1: tetrachloromethane; triphenylphosphine / acetonitrile / 1 h / 25 °C 2.1: 2.5 h / 150 °C 3.1: N,N'-dimethyl-N,N'-propyleneurea; n-butyllithium / tetrahydrofuran; hexanes / 0.67 h / 0 °C / Horner-Wadsworth-Emmons reaction 3.2: -78 - 0 °C 4.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / 1 h / 0 - 25 °C 5.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 1 h / 25 °C View Scheme

1.1: 2.5 h / 150 °C 2.1: N,N'-dimethyl-N,N'-propyleneurea; n-butyllithium / tetrahydrofuran; hexanes / 0.67 h / 0 °C / Horner-Wadsworth-Emmons reaction 2.2: -78 - 0 °C 3.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / 1 h / 0 - 25 °C 4.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 1 h / 25 °C View Scheme

1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / 1 h / 0 - 25 °C 2: manganese(IV) oxide; sodium carbonate / dichloromethane / 1 h / 25 °C View Scheme

1.1: N,N'-dimethyl-N,N'-propyleneurea; n-butyllithium / tetrahydrofuran; hexanes / 0.67 h / 0 °C / Horner-Wadsworth-Emmons reaction 1.2: -78 - 0 °C 2.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / 1 h / 0 - 25 °C 3.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 1 h / 25 °C View Scheme

1.1: 100 - 150 °C / Neat (no solvent) 2.1: N,N'-dimethyl-N,N'-propyleneurea; n-butyllithium / tetrahydrofuran; hexanes / 0.67 h / 0 °C / Horner-Wadsworth-Emmons reaction 2.2: -78 - 0 °C 3.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / 1 h / 0 - 25 °C 4.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 1 h / 25 °C View Scheme