T=150°C; Michaelis-Arbuzov reaction; 2.5 h; optical yield given as percent de;

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: water; sodium hydroxide / methanol; dimethyl sulfoxide / 2 h / 65 °C 3.2: 0 °C / pH 5 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

1.1: 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