triethylamine in hexane T=0 - 20°C;

immobilized Candida antarctica Lipase B in neat (no solvent) T=60°C; Green chemistryEnzymatic reaction;

immobilized Candida antarctica Lipase B in neat (no solvent) T=60°C; Green chemistryEnzymatic reaction;

4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine in dichloromethane T=20°C; Product distribution / selectivity;

1: 94 percent / KOH / diethyl ether / 4 h 2: EtMgBr, CuBr*Me2S / tetrahydrofuran / 1.) 50 deg C, 30 min; 0 deg C, 5 min, 2.) 0 deg C to r.t., 10 h 3: 1.) K3Fe(CN)6, K2CO3, OsO4, H2O, 2.) Dowex 50 x 8 - 100 ion-exchange resin / 1.) t-BuOH, r.t., 48 h, 2.) MeOH, r.t., 13 h 4: conc. H2SO4, molecular sieves 4A, Na2SO4 / 13 h / Ambient temperature 5: 87 percent / H2, ethylenediamine / P-2 Ni catalyst / ethanol / 5 h / 23 °C 6: 82 percent / pyridine / CH2Cl2 / 8 h / 0 °C 7: CaCO3 / acetonitrile / 48 h / 90 °C 8: 73 percent / NaHMDS / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) -78 deg C to r.t., 3 h 9: 90 percent / 4 N aq. HCl, methylene blue / tetrahydrofuran / 0.5 h 10: 0.8 M aq. NaIO4, 60-200 mesh SiO2 / CH2Cl2 / 0.08 h / Ambient temperature 11: NaHMDS / 1.) THF, -75 deg C, 2.) CH2Cl2, -75 deg C to r.t., 4 h View Scheme

1: conc. H2SO4, molecular sieves 4A, Na2SO4 / 13 h / Ambient temperature 2: 87 percent / H2, ethylenediamine / P-2 Ni catalyst / ethanol / 5 h / 23 °C 3: 82 percent / pyridine / CH2Cl2 / 8 h / 0 °C 4: CaCO3 / acetonitrile / 48 h / 90 °C 5: 73 percent / NaHMDS / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) -78 deg C to r.t., 3 h 6: 90 percent / 4 N aq. HCl, methylene blue / tetrahydrofuran / 0.5 h 7: 0.8 M aq. NaIO4, 60-200 mesh SiO2 / CH2Cl2 / 0.08 h / Ambient temperature 8: NaHMDS / 1.) THF, -75 deg C, 2.) CH2Cl2, -75 deg C to r.t., 4 h View Scheme

1: 87 percent / H2, ethylenediamine / P-2 Ni catalyst / ethanol / 5 h / 23 °C 2: 82 percent / pyridine / CH2Cl2 / 8 h / 0 °C 3: CaCO3 / acetonitrile / 48 h / 90 °C 4: 73 percent / NaHMDS / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) -78 deg C to r.t., 3 h 5: 90 percent / 4 N aq. HCl, methylene blue / tetrahydrofuran / 0.5 h 6: 0.8 M aq. NaIO4, 60-200 mesh SiO2 / CH2Cl2 / 0.08 h / Ambient temperature 7: NaHMDS / 1.) THF, -75 deg C, 2.) CH2Cl2, -75 deg C to r.t., 4 h View Scheme

1: 1.) K3Fe(CN)6, K2CO3, OsO4, H2O, 2.) Dowex 50 x 8 - 100 ion-exchange resin / 1.) t-BuOH, r.t., 48 h, 2.) MeOH, r.t., 13 h 2: conc. H2SO4, molecular sieves 4A, Na2SO4 / 13 h / Ambient temperature 3: 87 percent / H2, ethylenediamine / P-2 Ni catalyst / ethanol / 5 h / 23 °C 4: 82 percent / pyridine / CH2Cl2 / 8 h / 0 °C 5: CaCO3 / acetonitrile / 48 h / 90 °C 6: 73 percent / NaHMDS / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) -78 deg C to r.t., 3 h 7: 90 percent / 4 N aq. HCl, methylene blue / tetrahydrofuran / 0.5 h 8: 0.8 M aq. NaIO4, 60-200 mesh SiO2 / CH2Cl2 / 0.08 h / Ambient temperature 9: NaHMDS / 1.) THF, -75 deg C, 2.) CH2Cl2, -75 deg C to r.t., 4 h View Scheme

1: EtMgBr, CuBr*Me2S / tetrahydrofuran / 1.) 50 deg C, 30 min; 0 deg C, 5 min, 2.) 0 deg C to r.t., 10 h 2: 1.) K3Fe(CN)6, K2CO3, OsO4, H2O, 2.) Dowex 50 x 8 - 100 ion-exchange resin / 1.) t-BuOH, r.t., 48 h, 2.) MeOH, r.t., 13 h 3: conc. H2SO4, molecular sieves 4A, Na2SO4 / 13 h / Ambient temperature 4: 87 percent / H2, ethylenediamine / P-2 Ni catalyst / ethanol / 5 h / 23 °C 5: 82 percent / pyridine / CH2Cl2 / 8 h / 0 °C 6: CaCO3 / acetonitrile / 48 h / 90 °C 7: 73 percent / NaHMDS / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) -78 deg C to r.t., 3 h 8: 90 percent / 4 N aq. HCl, methylene blue / tetrahydrofuran / 0.5 h 9: 0.8 M aq. NaIO4, 60-200 mesh SiO2 / CH2Cl2 / 0.08 h / Ambient temperature 10: NaHMDS / 1.) THF, -75 deg C, 2.) CH2Cl2, -75 deg C to r.t., 4 h View Scheme

1: 81 percent / pyridine / CH2Cl2 / 13 h / Ambient temperature 2: acetonitrile / 13 h / Heating 3: NaHMDS / 1.) THF, -75 deg C, 2.) CH2Cl2, -75 deg C to r.t., 4 h View Scheme