1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 3.2: 15.75 h / 0 - 20 °C / Inert atmosphere 4.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

With  (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen in  dichloromethane T=0 - 22°C; P=750.075 Torr;  stereoselective reaction;   

Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere2: benzene / 24 h / Inert atmosphere; Reflux3: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere  

Multi-step reaction with 5 steps 1.1: tetrahydrofuran; water / 36 h / 0 - 20 °C / Inert atmosphere2.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere2.2: 6 h / 20 °C / Inert atmosphere3.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere4.1: benzene / 24 h / Inert atmosphere; Reflux5.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere  

Multi-step reaction with 3 steps 1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere2.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere3.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere3.2: 15.75 h / 0 - 20 °C / Inert atmosphere  

With  1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in  dimethyl sulfoxide T=22°C; 2.5 h;  Inert atmosphere;