1.1: tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C 1.2: tetrahydrofuran; pentane / -78 - 20 °C 2.1: 4-methylmorpholine N-oxide; mol sieves 4 Angstroem; tetrapropylammonium perruthenate / CH2Cl2 / 20 °C View Scheme

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C 2.2: 1.25 h / -78 °C 3.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 20 °C / |Molecular sieve View Scheme

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C 2.2: 1.25 h / -78 °C 3.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 20 °C / |Molecular sieve View Scheme

1.1: tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C 1.2: tetrahydrofuran; pentane / -78 - 20 °C 2.1: 4-methylmorpholine N-oxide; mol sieves 4 Angstroem; tetrapropylammonium perruthenate / CH2Cl2 / 20 °C View Scheme

1: 1.) tetra-n-butylammonium bisulfate, 50percent KOH / 1.) benzene, 5 min, 2.) 2 h 2: 1.) a) tert-butyllithium, b) cuprous cyanide / 1.) pentane, THF-Et2O 3:1 a) -95 deg C, 6 min b) -90 deg C, 3 min, 2.) a) -95 deg C, 0.5 h, b) -78 deg C, 1 h, c) RT, 14 h 3: lithium diisopropylamine / 1.) THF, hexane, -70 deg C, 1.5 h, 2.) -65 deg C to RT, 15 h View Scheme

1: 1.) a) tert-butyllithium, b) cuprous cyanide / 1.) pentane, THF-Et2O 3:1 a) -95 deg C, 6 min b) -90 deg C, 3 min, 2.) a) -95 deg C, 0.5 h, b) -78 deg C, 1 h, c) RT, 14 h 2: lithium diisopropylamine / 1.) THF, hexane, -70 deg C, 1.5 h, 2.) -65 deg C to RT, 15 h View Scheme

lithium diisopropyl amide 1.) THF, hexane, -70 deg C, 1.5 h, 2.) -65 deg C to RT, 15 h; Yield given. Multistep reaction;

tert.-butyl lithium; copper (I) cyanide 1.) pentane, THF-Et2O 3:1, a) -95 deg C, 6 min, b) 3 min, 2.) a) -95 deg C, 0.5 h, b) -78 deg C, 1 h, c) RT, 14 h; Yield given. Multistep reaction. Yields of byproduct given;