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

sodium tetrahydroborate in ethanol 2 h; Ambient temperature;

1: 67 percent / HCl(g) 2: 71 percent / NaBH4 / ethanol / 2 h / Ambient temperature View Scheme