tetrabutyl ammonium fluoride in tetrahydrofuran 12 h; Ambient temperature;

1: 1) n-BuLi / 1) THF, hexane, -60 deg C, 1h, 2) HMPA, RT, 36h 2: 3N HCl / methanol / 0.33 h / Ambient temperature 3: 41 percent / t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 4 h / -21 °C 5: 97 percent / imidazole / dimethylformamide 6: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 7: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: 95 percent / PPTS / CH2Cl2 / 1 h / Ambient temperature 2: 1) n-BuLi / 1) THF, hexane, -60 deg C, 1h, 2) HMPA, RT, 36h 3: 3N HCl / methanol / 0.33 h / Ambient temperature 4: 41 percent / t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 4 h / -21 °C 6: 97 percent / imidazole / dimethylformamide 7: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 8: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: 1) n-BuLi / 1) THF, hexane, -60 deg C, 1h, 2) HMPA, RT, 36h 2: 3N HCl / methanol / 0.33 h / Ambient temperature 3: 41 percent / t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 4 h / -21 °C 5: 97 percent / imidazole / dimethylformamide 6: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 7: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: 3N HCl / methanol / 0.33 h / Ambient temperature 2: 41 percent / t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 4 h / -21 °C 4: 97 percent / imidazole / dimethylformamide 5: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 6: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: 41 percent / t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 4 h / -21 °C 3: 97 percent / imidazole / dimethylformamide 4: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 5: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

2: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C 3: Br2 / CH2Cl2 / 0.17 h / -70 °C 4: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C 5: imidazole / dimethylformamide / 5 h / Ambient temperature 6: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 7: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 8: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 9: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: imidazole / dimethylformamide / 5 h / Ambient temperature 2: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 3: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 4: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 5: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 2: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 2: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 3: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 4: 55 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature View Scheme