1: 5-hexen-1-yl azide With lithium aluminium tetrahydride in diethyl ether 2: di-tert-butyl dicarbonate in diethyl ether; water

1: aq. K2OsO4, (DHQD)2PYR, K3Fe(CN)6, K2CO3 / 2-methyl-propan-2-ol / 24 h / 0 °C 2: 1.) pyridinium p-toluenesulfonate, trimethyl orthoacetate, 2.) acetyl bromide, 3.) potassium carbonate View Scheme

1: LiAlH4 2: p-TsOH, Et3N 3: POCl3, Et3N 4: 3 percent Chromat. / (Me3Si)3SiH, AIBN / toluene / 70 °C View Scheme

1: LiAlH4 2: p-TsOH, Et3N 3: POCl3, Et3N 4: 2 percent Chromat. / (Me3Si)3SiH, AIBN / toluene / 70 °C View Scheme

1: LiAlH4 2: p-TsOH, Et3N 3: POCl3, Et3N 4: 86 percent Chromat. / (Me3Si)3SiH, AIBN / toluene / 70 °C View Scheme

lithium aluminium tetrahydride

1.1: triphenylphosphine / tetrahydrofuran; water / 15 h 1.2: 12 h 2.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 5 h / 20 °C 3.1: Jorgensen's catalyst / methanol; 1,2-dichloro-ethane / 240 h / -25 °C 4.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C View Scheme

1: LiAlH4 2: p-TsOH, Et3N 3: POCl3, Et3N View Scheme

Multi-step reaction with 3 steps 1.1: triphenylphosphine / tetrahydrofuran; water / 15 h1.2: 12 h2.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 5 h / 20 °C3.1: Jorgensen's catalyst / methanol; 1,2-dichloro-ethane / 240 h / -25 °C