Multi-step reaction with 9 steps
1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
2.1: 3,3-dimethyldioxirane / dichloromethane / -78 - 0 °C / Inert atmosphere
2.2: 1.17 h / -78 - 0 °C / Inert atmosphere
2.3: 0 °C
3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve
4.1: diethyl ether; toluene / 0.67 h / -78 - 0 °C / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: pyridinium p-toluenesulfonate / methanol / 3 h / 65 °C / Inert atmosphere
7.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
7.2: 0.5 h / -78 - 20 °C / Inert atmosphere
8.1: copper(l) iodide / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere
8.2: 2 h / -40 °C / Inert atmosphere
9.1: camphor-10-sulfonic acid / methanol / 1 h / 0 - 20 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; dmap; copper(l) iodide; tetrapropylammonium perruthennate; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja200089f