1,8-diazabicyclo[5.4.0]undec-7-ene in toluene T=100°C; 18 h;

1: 100 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 2: imidazole / dimethylformamide / 12 h / Ambient temperature 3: 90 percent / Ley's tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, molecular sieves / CH2Cl2 / 0.25 h / Ambient temperature 4: 1.) LDA, HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT, 4 h 5: 96 percent / PdCl2, CuCl, air / dimethylformamide; H2O / 4.5 h / Ambient temperature 6: 84 percent / NaHMDS, HMPA / tetrahydrofuran / 0.67 h / -78 - -50 °C / a) -78 deg C. 15 min, b) 0 deg C, 15 min, c) 50 deg C, 10 min 7: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 8: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 9: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 10: NaBH4 / methanol / 2 h / Ambient temperature 11: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 12: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 13: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 14: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 15: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme

1: 96 percent / PdCl2, CuCl, air / dimethylformamide; H2O / 4.5 h / Ambient temperature 2: 84 percent / NaHMDS, HMPA / tetrahydrofuran / 0.67 h / -78 - -50 °C / a) -78 deg C. 15 min, b) 0 deg C, 15 min, c) 50 deg C, 10 min 3: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 4: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 5: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 6: NaBH4 / methanol / 2 h / Ambient temperature 7: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 8: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 9: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 10: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 11: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme

1: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 2: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 3: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 4: NaBH4 / methanol / 2 h / Ambient temperature 5: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 6: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 7: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 8: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 9: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme

1: 84 percent / NaHMDS, HMPA / tetrahydrofuran / 0.67 h / -78 - -50 °C / a) -78 deg C. 15 min, b) 0 deg C, 15 min, c) 50 deg C, 10 min 2: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 3: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 4: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 5: NaBH4 / methanol / 2 h / Ambient temperature 6: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 7: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 8: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 9: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 10: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme

1: 1.) LDA, HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT, 4 h 2: 96 percent / PdCl2, CuCl, air / dimethylformamide; H2O / 4.5 h / Ambient temperature 3: 84 percent / NaHMDS, HMPA / tetrahydrofuran / 0.67 h / -78 - -50 °C / a) -78 deg C. 15 min, b) 0 deg C, 15 min, c) 50 deg C, 10 min 4: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 5: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 6: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 7: NaBH4 / methanol / 2 h / Ambient temperature 8: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 9: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 10: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 11: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 12: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme

1: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 2: NaBH4 / methanol / 2 h / Ambient temperature 3: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 4: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 5: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 6: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 7: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme

1: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 2: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 3: NaBH4 / methanol / 2 h / Ambient temperature 4: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 5: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 6: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 7: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 8: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme

1: NaBH4 / methanol / 2 h / Ambient temperature 2: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 3: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 4: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 5: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 6: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme

1: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 2: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme