sodium hydroxide in methanol T=40°C; 3 h;

phosphate buffer (pH=ca. 7); water T=10 - 30°C; activation parameters: ΔS(excit.), ΔG(excit.), E investigated; depends on cyclodextrin and phosphate buffer concentration, pH, solvent and temperature; KineticsThermodynamic data;

1: 59 percent / NaBH4 / methanol / 0.67 h / 0 °C 2: 17 percent / 2) NH4OAc, 25percent aq. TiCl3 / 1) MeOH; 2) H2O, MeOH 3: 96 percent / hydrogen fluoride, pyridine / acetonitrile / 1 h / Ambient temperature 4: 84 percent / 5N NaOH / methanol / 6 h / 20 - 40 °C View Scheme

1: 51 percent / sodium nitrite, phloroglucinol / dimethylsulfoxide / 20 h / Ambient temperature 2: 1) 3N sodium hydroxide; 3) acetic acid / 1) H2O, 0 deg C, 3 h; 2) H2O, 0 deg C, 5 h; 3) H2O, room temp., 20 h 3: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 4: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 5: 59 percent / NaBH4 / methanol / 0.67 h / 0 °C 6: 17 percent / 2) NH4OAc, 25percent aq. TiCl3 / 1) MeOH; 2) H2O, MeOH 7: 96 percent / hydrogen fluoride, pyridine / acetonitrile / 1 h / Ambient temperature 8: 84 percent / 5N NaOH / methanol / 6 h / 20 - 40 °C View Scheme

1: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 2: 59 percent / NaBH4 / methanol / 0.67 h / 0 °C 3: 17 percent / 2) NH4OAc, 25percent aq. TiCl3 / 1) MeOH; 2) H2O, MeOH 4: 96 percent / hydrogen fluoride, pyridine / acetonitrile / 1 h / Ambient temperature 5: 84 percent / 5N NaOH / methanol / 6 h / 20 - 40 °C View Scheme

1: 1) 3N sodium hydroxide; 3) acetic acid / 1) H2O, 0 deg C, 3 h; 2) H2O, 0 deg C, 5 h; 3) H2O, room temp., 20 h 2: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 3: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 4: 59 percent / NaBH4 / methanol / 0.67 h / 0 °C 5: 17 percent / 2) NH4OAc, 25percent aq. TiCl3 / 1) MeOH; 2) H2O, MeOH 6: 96 percent / hydrogen fluoride, pyridine / acetonitrile / 1 h / Ambient temperature 7: 84 percent / 5N NaOH / methanol / 6 h / 20 - 40 °C View Scheme

1: 96 percent / hydrogen fluoride, pyridine / acetonitrile / 1 h / Ambient temperature 2: 84 percent / 5N NaOH / methanol / 6 h / 20 - 40 °C View Scheme

1: 17 percent / 2) NH4OAc, 25percent aq. TiCl3 / 1) MeOH; 2) H2O, MeOH 2: 96 percent / hydrogen fluoride, pyridine / acetonitrile / 1 h / Ambient temperature 3: 84 percent / 5N NaOH / methanol / 6 h / 20 - 40 °C View Scheme

1: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 2: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 3: 59 percent / NaBH4 / methanol / 0.67 h / 0 °C 4: 17 percent / 2) NH4OAc, 25percent aq. TiCl3 / 1) MeOH; 2) H2O, MeOH 5: 96 percent / hydrogen fluoride, pyridine / acetonitrile / 1 h / Ambient temperature 6: 84 percent / 5N NaOH / methanol / 6 h / 20 - 40 °C View Scheme

1: 96 percent / hydrogen fluoride, pyridine / acetonitrile / 1 h / Ambient temperature 2: 84 percent / 5N NaOH / methanol / 6 h / 20 - 40 °C View Scheme