1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 1.2: -78 - 20 °C 2.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 4.5 h / 20 °C View Scheme

1: 89 percent / NaN(SiMe3)2 / tetrahydrofuran / 2 h / -78 °C 2: 89 percent / H2O2; LiOH / tetrahydrofuran; H2O / 1.5 h / 0 °C 3: 74 percent / Et3N; DPPA / toluene / 6.5 h / Heating 4: 91 percent / Me2S / CH2Cl2; trifluoroacetic acid / 3 h / 20 °C View Scheme

1: 1.) diisopropylethylamine, dibutylboryl triflate (n-Bu2BOTf), 2.) N-bromosuccinimide (NBS) / 1.) CH2Cl2, a.) -78 deg C, 15 min, b.) 0 deg C, 1 h, 2.) -78 deg C, 1 h 2: tetramethylguanidinium azide (TMGA) / CH2Cl2 / 1 h / -23 °C 3: 97 percent / lithium hydroxide / tetrahydrofuran; H2O / 0.5 h / 0 °C 4: 97 percent / H2 / 10percent Pd/C / H2O; acetic acid / 3 h / 760 Torr View Scheme

lanthanum(III) iodide in tetrahydrofuran Ambient temperature;

Multi-step reaction with 2 steps 1: 89 percent / NaN(SiMe3)2 / tetrahydrofuran / 2 h / -78 °C2: 89 percent / H2O2; LiOH / tetrahydrofuran; H2O / 1.5 h / 0 °C  

With  N-bromosuccinmide; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine  1.) CH2Cl2, a.) -78 deg C, 15 min, b.) 0 deg C, 1 h, 2.) -78 deg C, 1 h;  Multistep reaction;   

Multi-step reaction with 2 steps 1: 1.) Bu2BOTf, R3N, 2.) NBS / 2.) CH2Cl2, -78 deg C, 75 min.2: tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C / var.: NaN3, DMF or DMSO, 0 deg C