Multi-step reaction with 6 steps
1: 99 percent / Br2 / diethyl ether / 0.5 h / 0 °C
2: 71 percent / LDA / tetrahydrofuran / 1.) 0 deg C, 3 h, 2.) room temperature, overnight
3: 88 percent / (Ph3P)3Pd, CuI, i-Pr2NH / 15 h / Ambient temperature
4: 41 percent / Li, 1,3-diaminopropane, t-BuOK / 20 h / 65 °C
5: 97 percent / imidazole, DMAP / dimethylformamide / 15 h / Ambient temperature
6: 1.) Me3Al, Cp2ZrCl2, 2.) MeLi / 1.) 1,2-dichloroethane, hexane, overnight, 2.) hexane, room temperature, 20 h
With
1H-imidazole; dmap; copper(l) iodide; zirconocene dichloride; tris(triphenylphosphano)palladium; potassium tert-butylate; methyllithium; bromine; trimethylaluminum; lithium; Trimethylenediamine; diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo982260t