Multi-step reaction with 5 steps
1: 1.) TMEDA, 1.4 M sec-butyllithium / 1.) THF, cyclohexane, -78 deg C, 1 h, 2.) THF, cyclohexane, -78 deg C, 1 h
2: 1.) 2.5 M n-butyllithium / 1.) THF, hexanes, -78 deg C, 30 min, 2.) THF, hexanes, 15 min
3: NaBH4 / methanol / 0.5 h / 0 °C
4: racemic camphorsulfonic acid / toluene / 24 h / Heating
5: DBU / various solvent(s) / 135 °C
With
sodium tetrahydroborate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; camphor-10-sulfonic acid; sec.-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
methanol; toluene;
DOI:10.1021/jo00280a054