sodium hydride T=20°C;

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=0°C; Inert atmosphere;

1: (E)-cinnamaldehyde With hexafluoroisopropyl alcohol; 3,3',5,5'-tetra-tert-butyl-4,4'-diphenoquinone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1H-1,2,4-triazol-4-ium iodide in tetrahydrofuran T=20°C; 2 h; Inert atmosphere; 2: 1-amino-2-propene in tetrahydrofuran T=20°C; 6 h; Inert atmosphere;

1: isopropyl alcohol; 1-amino-2-propene With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1H-1,2,4-triazol-4-ium iodide in tetrahydrofuran 0.0833333 h; Inert atmosphere; 2: (E)-cinnamaldehyde With 3,3',5,5'-tetra-tert-butyl-4,4'-diphenoquinone in tetrahydrofuran T=20°C; 1 h; Inert atmosphere; chemoselective reaction;

1: SOCl2 / 2 h / 20 °C 2: TEA; DMAP / petroleum ether / 15 h / 20 °C View Scheme

1: 80 percent / diethyl ether / 1 h / Ambient temperature 2: 88 percent / 25percent aq. sodium sulfite, 10percent aq. KOH / diethyl ether; CHCl3 / 1 h 3: 69 percent / KOH, DMSO / 23 h 4: 14 percent / 144 h / 90 °C View Scheme

1: 88 percent / 25percent aq. sodium sulfite, 10percent aq. KOH / diethyl ether; CHCl3 / 1 h 2: 69 percent / KOH, DMSO / 23 h 3: 14 percent / 144 h / 90 °C View Scheme

4-methyl-morpholine; isobutyl chloroformate 1.) THF, -15 deg C, 30 min, 2.) 4 deg C, 15 h; Yield given. Multistep reaction;

T=90°C; 144 h;

1: 69 percent / KOH, DMSO / 23 h 2: 14 percent / 144 h / 90 °C View Scheme