1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr 2: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C 3: KOH / ethane-1,2-diol; H2O / 20 h / 100 °C View Scheme

1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C 2: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr 3: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C 4: KOH / ethane-1,2-diol; H2O / 20 h / 100 °C View Scheme

1.1: magnesium / tetrahydrofuran / 25 °C 1.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C 1.3: tetrahydrofuran / 0.67 h / -50 - 0 °C 2.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C 3.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr 4.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C 5.1: KOH / ethane-1,2-diol; H2O / 20 h / 100 °C View Scheme

1.1: 79 percent / tributylphosphine; N,N-diisopropylethylamine / CH2Cl2; 2-methyl-propan-2-ol / 3 h / 25 °C 2.1: 86 percent / CH2Cl2 / 18 h / 25 °C 3.1: 95 percent / borane dimethyl sulfide complex / (S)-2-methyl-CBS-oxazaborolidine catalyst / CH2Cl2; tetrahydrofuran; toluene / 2 h / -20 °C 4.1: 89 percent / pyridine; DMAP / CH2Cl2 / 2 h / 25 °C 5.1: magnesium / tetrahydrofuran / 25 °C 5.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C 5.3: tetrahydrofuran / 0.67 h / -50 - 0 °C 6.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C 7.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr 8.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C 9.1: KOH / ethane-1,2-diol; H2O / 20 h / 100 °C View Scheme

1.1: 79 percent / tributylphosphine; N,N-diisopropylethylamine / CH2Cl2; 2-methyl-propan-2-ol / 3 h / 25 °C 2.1: 86 percent / CH2Cl2 / 18 h / 25 °C 3.1: 95 percent / borane dimethyl sulfide complex / (S)-2-methyl-CBS-oxazaborolidine catalyst / CH2Cl2; tetrahydrofuran; toluene / 2 h / -20 °C 4.1: 89 percent / pyridine; DMAP / CH2Cl2 / 2 h / 25 °C 5.1: magnesium / tetrahydrofuran / 25 °C 5.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C 5.3: tetrahydrofuran / 0.67 h / -50 - 0 °C 6.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C 7.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr 8.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C 9.1: KOH / ethane-1,2-diol; H2O / 20 h / 100 °C View Scheme

1.1: NaOMe / methanol / 3 h / 63 - 66 °C 2.1: 89.7 percent / H2 / Raney-Co / toluene; methanol / 1 h / 90 - 100 °C / 9880 - 12160 Torr 3.1: NaOMe / toluene / 0.5 h / 70 - 80 °C 4.1: LiAlH4 / toluene; tetrahydrofuran / 2 h / 73 - 75 °C 4.2: via salt with L-o-chlorotartranilic acid/Celite 5.1: aq. NaOH / toluene / 2 h / 45 - 55 °C 6.1: Et3N / toluene / 1.25 h / 22 - 25 °C 7.1: NaOMe / toluene / 5.5 h / Heating 8.1: HCl / propan-2-ol / 2.5 h / 71 - 75 °C View Scheme

1.1: 89.7 percent / H2 / Raney-Co / toluene; methanol / 1 h / 90 - 100 °C / 9880 - 12160 Torr 2.1: NaOMe / toluene / 0.5 h / 70 - 80 °C 3.1: LiAlH4 / toluene; tetrahydrofuran / 2 h / 73 - 75 °C 3.2: via salt with L-o-chlorotartranilic acid/Celite 4.1: aq. NaOH / toluene / 2 h / 45 - 55 °C 5.1: Et3N / toluene / 1.25 h / 22 - 25 °C 6.1: NaOMe / toluene / 5.5 h / Heating 7.1: HCl / propan-2-ol / 2.5 h / 71 - 75 °C View Scheme

1.1: NaOMe / toluene / 0.5 h / 70 - 80 °C 2.1: LiAlH4 / toluene; tetrahydrofuran / 2 h / 73 - 75 °C 2.2: via salt with L-o-chlorotartranilic acid/Celite 3.1: aq. NaOH / toluene / 2 h / 45 - 55 °C 4.1: Et3N / toluene / 1.25 h / 22 - 25 °C 5.1: NaOMe / toluene / 5.5 h / Heating 6.1: HCl / propan-2-ol / 2.5 h / 71 - 75 °C View Scheme

1.1: toluene / 3.75 h / 100 - 105 °C / Large scale reaction 1.2: 1 h / 60 °C 1.3: 25 - 35 °C 2.1: water; sodium hydroxide / isopropyl alcohol / 82 - 85 °C / Large scale reaction 3.1: hydrogenchloride / ethyl acetate / 0 - 35 °C View Scheme

1.1: di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; Jorgensen's catalyst; trichloroacetic acid / 1,2-dichloro-ethane / 20 °C / |Inert atmosphere 2.1: sodium tetrahydroborate / dichloromethane; ethanol / 0.33 h / -78 °C / |Inert atmosphere 3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 10 h / 85 °C / |Inert atmosphere 4.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 4.2: 1 h / 20 °C / |Inert atmosphere 5.1: hydrazine hydrate / ethanol / 0.58 h / 20 - 85 °C / |Inert atmosphere 6.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 2.5 h / 20 °C / |Inert atmosphere 7.1: hydrogenchloride / dichloromethane; methanol / 0 °C / |Inert atmosphere View Scheme