Multi-step reaction with 13 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
10.1: potassium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere
10.2: 5 h / 0 - 20 °C / Inert atmosphere
11.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol / 16 h / 20 °C / Inert atmosphere
12.1: lead(IV) tetraacetate / benzene / 1 h / 20 °C / Inert atmosphere
13.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene; water / tert-butyl alcohol / 3 h / 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; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; osmium(VIII) oxide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; camphor-10-sulfonic acid; water; lead(IV) tetraacetate; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; potassium hydride; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; mineral oil; tert-butyl alcohol; benzene;
DOI:10.1021/ja200089f