1: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, 2.) CH2Cl2, -20 deg C, 14 h 2: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating 3: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating 4: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 5: 94 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 6: 92 percent / H2 / 10percent Pd on C / methanol / 2 h / 760 Torr 7: 90 percent / conc. HCl / methanol / 1 h / Heating View Scheme

With  diisobutylaluminium hydride in  dichloromethane; toluene 14 h;  Ambient temperature;   

Multi-step reaction with 3 steps 1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 to 0 deg C2: NaH / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) 0 deg C to r.t., 2 h3: 87 percent / DIBALH / tetrahydrofuran; toluene / 2 h / -78 °C  

With  titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate  

Multi-step reaction with 2 steps 1: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, 2.) CH2Cl2, -20 deg C, 14 h2: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating  

Multi-step reaction with 3 steps 1: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, 2.) CH2Cl2, -20 deg C, 14 h2: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating3: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating  

Multi-step reaction with 4 steps 1: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, 2.) CH2Cl2, -20 deg C, 14 h2: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating3: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating4: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature  

Multi-step reaction with 5 steps 1: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, 2.) CH2Cl2, -20 deg C, 14 h2: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating3: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating4: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature5: 94 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C  

Multi-step reaction with 6 steps 1: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, 2.) CH2Cl2, -20 deg C, 14 h2: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating3: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating4: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature5: 94 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C6: 92 percent / H2 / 10percent Pd on C / methanol / 2 h / 760 Torr