1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere 3: triphenylphosphine; diethylazodicarboxylate / diethyl ether; benzene / 14 h / 20 °C 4: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 5: RuCl2(tricyclohexylphosphine)2(benzylidene) / toluene / 23 h / 80 °C / Inert atmosphere 6: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 7: aluminium(III) iodide; tetra-(n-butyl)ammonium iodide / benzene / 10 °C View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 &deg;C<br />2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 &deg;C / Inert atmosphere<br />3.1: magnesium / tetrahydrofuran / 0.5 h / 20 - 25 &deg;C / Inert atmosphere<br />3.2: 1 h / Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: (R,R)-Co-salen; acetic acid / water; toluene / 20 &deg;C / Cooling with ice<br />2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 &deg;C / Inert atmosphere<br />3.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 4 h / 0 - 25 &deg;C / Inert atmosphere<br />4.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 &deg;C<br />5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 &deg;C / Inert atmosphere<br />6.1: magnesium / tetrahydrofuran / 0.5 h / 20 - 25 &deg;C / Inert atmosphere<br />6.2: 1 h / Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 25 &deg;C / Inert atmosphere<br />2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 &deg;C / Inert atmosphere<br />3.1: (R,R)-Co-salen; acetic acid / water; toluene / 20 &deg;C / Cooling with ice<br />4.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 &deg;C / Inert atmosphere<br />5.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 4 h / 0 - 25 &deg;C / Inert atmosphere<br />6.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 &deg;C<br />7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 &deg;C / Inert atmosphere<br />8.1: magnesium / tetrahydrofuran / 0.5 h / 20 - 25 &deg;C / Inert atmosphere<br />8.2: 1 h / Inert atmosphere<br /> <br /> &nbsp;