Wilkinson's catalyst in water; acetonitrile deallylation; 5 h; Heating;

sodium tetrahydroborate in methanol T=-78°C; 4 h;

1: 96 percent / α,α-diphenyl-2-pyrrolidine methanol; B(OMe)3; BH3*SMe2 / tetrahydrofuran / 1 h / 20 °C 2: 82 percent / Et3N / CH2Cl2 / 1.75 h / -20 °C 3: 75 percent / 14 h / 0 °C 4: 89 percent / (Ph3P)3RhCl / acetonitrile; H2O / 5 h / Heating View Scheme

1: 82 percent / Et3N / CH2Cl2 / 1.75 h / -20 °C 2: 75 percent / 14 h / 0 °C 3: 89 percent / (Ph3P)3RhCl / acetonitrile; H2O / 5 h / Heating View Scheme

1: 75 percent / 14 h / 0 °C 2: 89 percent / (Ph3P)3RhCl / acetonitrile; H2O / 5 h / Heating View Scheme

1: in tetrahydrofuran T=20°C; 3 h; Inert atmosphere; 2: With hydrogen in tetrahydrofuran; water P=750.075 Torr; 18 h; Inert atmosphere; Reagent/catalystSolvent; diastereoselective reaction;

1: hydroxymethanesulfinic acid sodium salt / N,N-dimethyl-formamide / 23 h / 20 °C / Inert atmosphere 2: boric acid trimethyl ester; (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol; dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 20 °C 3: triethylamine / dichloromethane / 3 h / -20 °C / Inert atmosphere 4: dichloromethane / -20 - 20 °C 5: Wilkinson's catalyst / water; acetonitrile / 5 h / 100 °C / Inert atmosphere View Scheme

1: zinc(II) iodide / toluene / 3 h / 120 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 4 h / -78 °C View Scheme

1.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / toluene / 2.5 h / 60 °C / |Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / ethanol / 2.5 h / 20 °C / 750.08 Torr 3.1: tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 3.2: Raney nickel / 18 h / 750.08 Torr / |Inert atmosphere View Scheme

1.1: palladium 10 on activated carbon; hydrogen / ethanol / 2.5 h / 20 °C / 750.08 Torr 2.1: tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 2.2: Raney nickel / 18 h / 750.08 Torr / |Inert atmosphere View Scheme