hydrogenchloride in tetrahydrofuran 3 h; Heating;

1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C 1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis 1.3: 76 percent / aq. NaOH; aq. H2O2 / 3 h / Heating 2.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 3.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C 4.1: Ph3P / tetrahydrofuran 4.2: 66 percent / H2O 5.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 6.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 8.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 9.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 10.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 11.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme

1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C 1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis 1.3: 76 percent / aq. NaOH; aq. H2O2 / 3 h / Heating 2.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 3.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C 4.1: Ph3P / tetrahydrofuran 4.2: 66 percent / H2O 5.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 6.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 8.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 9.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 10.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 11.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme

1.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 2.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C 3.1: Ph3P / tetrahydrofuran 3.2: 66 percent / H2O 4.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 5.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 6.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 7.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 8.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 9.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 10.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme

1.1: Ph3P / tetrahydrofuran 1.2: 66 percent / H2O 2.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 3.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 4.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 5.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 6.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 7.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 8.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme

1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 2: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 3: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 4: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 5: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 6: 50 percent / DDQ / dioxane / 4 h / 110 °C 7: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme

1.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C 2.1: Ph3P / tetrahydrofuran 2.2: 66 percent / H2O 3.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 4.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 5.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 6.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 7.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 8.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 9.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme

1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 2: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 3: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 4: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 5: 50 percent / DDQ / dioxane / 4 h / 110 °C 6: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme

camphor-10-sulfonic acid

1: 50 percent / DDQ / dioxane / 4 h / 110 °C 2: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme