Multi-step reaction with 6 steps
1: 1.) NaHMDS, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C
2: 1.) AlMe3 / 1.) CH2Cl2, toluene, 25 deg C, 30 min, 2.) CH2Cl2, toluene, reflux, 24 h
3: 1.) NaH / 1.) DMF, THF, 15 min, 2.) DMF, THF, 5 min
4: 93 percent / DIBAL-H / toluene / -78 °C
5: 71 percent / MgBr2*Et2O / CH2Cl2 / 1 h / -20 °C
6: 98 percent / 2,6-lutidine / CH2Cl2 / 0 °C
With
2,6-dimethylpyridine; trimethylaluminum; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; N-(benzenesulfonyl)-3-phenyloxaziridine; magnesium bromide;
In
dichloromethane; toluene;
DOI:10.1021/ja00050a024