Multi-step reaction with 10 steps
1: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere
2: toluene-4-sulfonic acid / methanol / 14 h / 20 °C / Inert atmosphere
3: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere
5: tris-(dibenzylideneacetone)dipalladium(0); (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol / tert-butyl methyl ether; hexane / 6 h / 40 °C
6: potassium hydroxide / methanol / 3.5 h / Inert atmosphere; Reflux
7: trichlorophosphate / toluene / 0.5 h / Inert atmosphere; Reflux
8: sodium tetrahydroborate / methanol / 3 h / 0 °C / Inert atmosphere
9: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere
10: sodium carbonate / dichloromethane / 12 h / 20 °C / Inert atmosphere
With
1H-imidazole; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); iodine; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol; potassium hydroxide; trichlorophosphate;
In
methanol; hexane; dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide; toluene;
7: |Bischler-Napieralski Reaction;
DOI:10.1039/c4cc01843e