potassium hydride; 1,3-diamino-propane T=20°C; Zipper reaction; 6 h;

potassium hydroxide in methanol

potassium tert-butylate; lithium; 1,3-diamino-propane T=20°C; 0.5 h;

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C 1.2: 59 percent / tetrahydrofuran / -78 - 20 °C 2.1: 78 percent / monotosyl (R,R)-1,2-diphenylethylene-1,2-diamine; KOH / [RuCl2(p-cymene)]2 / propan-2-ol / 40 h / 20 °C 3.1: 73 percent / lithium; 1,3-diaminopropane; potassium tert-butoxide / 0.5 h / 20 °C View Scheme

1: 78 percent / monotosyl (R,R)-1,2-diphenylethylene-1,2-diamine; KOH / [RuCl2(p-cymene)]2 / propan-2-ol / 40 h / 20 °C 2: 73 percent / lithium; 1,3-diaminopropane; potassium tert-butoxide / 0.5 h / 20 °C View Scheme

1: 1.) 1.55M nBuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, HMPT, -20 deg C, 10 min; r.t., 16 h 2: 50 percent / 80percent NaH, 1,3-propanediamine / 16 h / 60 °C View Scheme

1.1: 50 percent / sodium hydride / dimethylformamide / 0 °C 2.1: 93 percent / oxalyl chloride; DMSO / CH2Cl2 / 1.5 h / -78 °C 3.1: (+)-TADDOL; Ti(O-i-Pr)4 / toluene; hexane / 12 h / -25 °C 4.1: triethylamine; DMAP / CH2Cl2 / 20 h / 20 °C 5.1: water; DDQ / CH2Cl2 / 1 h / 20 °C 6.1: 2-iodoxybenzoic acid / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 20 °C 7.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C 7.2: tetrahydrofuran / -78 - 20 °C 8.1: potassium hydroxide / methanol / 3 h / 20 °C View Scheme

1.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C 1.2: tetrahydrofuran / -78 - 20 °C 2.1: potassium hydroxide / methanol / 3 h / 20 °C View Scheme

1.1: (+)-TADDOL; Ti(O-i-Pr)4 / toluene; hexane / 12 h / -25 °C 2.1: triethylamine; DMAP / CH2Cl2 / 20 h / 20 °C 3.1: water; DDQ / CH2Cl2 / 1 h / 20 °C 4.1: 2-iodoxybenzoic acid / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 20 °C 5.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C 5.2: tetrahydrofuran / -78 - 20 °C 6.1: potassium hydroxide / methanol / 3 h / 20 °C View Scheme

1.1: 2-iodoxybenzoic acid / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 20 °C 2.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C 2.2: tetrahydrofuran / -78 - 20 °C 3.1: potassium hydroxide / methanol / 3 h / 20 °C View Scheme