Multi-step reaction with 6 steps
1: 1.) Ti(O-i-Pr)4, t-BuOOH, 4A-molecular sieves, diisopropyl D-tartarate / 1.) CH2Cl2, 2,2,4-trimethylpentane, -20 deg C, 30 min, 2.) CH2Cl2, 2,2,4-trimethylpentane, -20 deg C, 11 h
2: 63 percent / Ti(O-i-Pr)4 / CH2Cl2 / 40 h / Ambient temperature
3: 80 percent / 2,6-lutidine / CH2Cl2 / 1 h / -20 °C
4: 84 percent / NaI, Proton Sponge / 1,2-dimethoxy-ethane / 24 h / Ambient temperature
5: 86 percent / MeLi / diethyl ether / 0.5 h / 0 °C
6: 1.) (SOCl)2, DMSO, 2.) pyridine / 1.) CH2Cl2, -60 deg C, 15 min, 2.) CH2Cl2, from -60 deg C to RT, 1 h
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; thionyl chloride; Proton Sponge; 4 A molecular sieve; methyllithium; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; sodium iodide;
In
1,2-dimethoxyethane; diethyl ether; dichloromethane;
DOI:10.1021/ja00090a016