ammonia in methanol T=0 - 20°C; 33 - 39 h; Product distribution / selectivity;

1.1: potassium carbonate / acetonitrile / 0.08 h 1.2: 2 h / 50 - 55 °C 2.1: potassium hydroxide; water / tetrahydrofuran; methanol / 36 h / 20 - 25 °C 3.1: thionyl chloride / 3 h / 65 °C / Inert atmosphere 3.2: 0 - 25 °C 4.1: tetrahydrofuran / -78 - 25 °C 5.1: 2,6-di-tert-butyl-4-methyl-phenol / [Cu(I)(CH3CN)4]PF6; (S,S)-i-Pr-FOXAP / tetrahydrofuran / -78 °C / Inert atmosphere 5.2: -78 °C 6.1: hydrogen; acetic acid / 5 Pd(II)/C(eggshell) / ethanol / 2 h / 15 - 20 °C / 2585.81 Torr / Inert atmosphere 6.2: 24 h / 15 - 20 °C View Scheme

1.1: potassium carbonate / acetonitrile / 0.08 h 1.2: 2 h / 50 - 55 °C 2.1: potassium hydroxide; water / tetrahydrofuran; methanol / 36 h / 20 - 25 °C 3.1: thionyl chloride / 3 h / 65 °C / Inert atmosphere 3.2: 0 - 25 °C 4.1: tetrahydrofuran / -78 - 25 °C 5.1: 2,6-di-tert-butyl-4-methyl-phenol / [Cu(I)(CH3CN)4]PF6; (S,S)-i-Pr-FOXAP / tetrahydrofuran / -78 °C / Inert atmosphere 5.2: -78 °C 6.1: hydrogen; acetic acid / 5 Pd(II)/C(eggshell) / ethanol / 2 h / 15 - 20 °C / 2585.81 Torr / Inert atmosphere 6.2: 24 h / 15 - 20 °C View Scheme

1.1: tetrahydrofuran / -78 - 25 °C 2.1: 2,6-di-tert-butyl-4-methyl-phenol / [Cu(I)(CH3CN)4]PF6; (S,S)-i-Pr-FOXAP / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: -78 °C 3.1: hydrogen; acetic acid / 5 Pd(II)/C(eggshell) / ethanol / 2 h / 15 - 20 °C / 2585.81 Torr / Inert atmosphere 3.2: 24 h / 15 - 20 °C View Scheme

1.1: 2,6-di-tert-butyl-4-methyl-phenol / [Cu(I)(CH3CN)4]PF6; (S,S)-i-Pr-FOXAP / tetrahydrofuran / -78 °C / Inert atmosphere 1.2: -78 °C 2.1: hydrogen; acetic acid / 5 Pd(II)/C(eggshell) / ethanol / 2 h / 15 - 20 °C / 2585.81 Torr / Inert atmosphere 2.2: 24 h / 15 - 20 °C View Scheme

1.1: potassium hydroxide; water / tetrahydrofuran; methanol / 36 h / 20 - 25 °C 2.1: thionyl chloride / 3 h / 65 °C / Inert atmosphere 2.2: 0 - 25 °C 3.1: tetrahydrofuran / -78 - 25 °C 4.1: 2,6-di-tert-butyl-4-methyl-phenol / [Cu(I)(CH3CN)4]PF6; (S,S)-i-Pr-FOXAP / tetrahydrofuran / -78 °C / Inert atmosphere 4.2: -78 °C 5.1: hydrogen; acetic acid / 5 Pd(II)/C(eggshell) / ethanol / 2 h / 15 - 20 °C / 2585.81 Torr / Inert atmosphere 5.2: 24 h / 15 - 20 °C View Scheme

1.1: thionyl chloride / 3 h / 65 °C / Inert atmosphere 1.2: 0 - 25 °C 2.1: tetrahydrofuran / -78 - 25 °C 3.1: 2,6-di-tert-butyl-4-methyl-phenol / [Cu(I)(CH3CN)4]PF6; (S,S)-i-Pr-FOXAP / tetrahydrofuran / -78 °C / Inert atmosphere 3.2: -78 °C 4.1: hydrogen; acetic acid / 5 Pd(II)/C(eggshell) / ethanol / 2 h / 15 - 20 °C / 2585.81 Torr / Inert atmosphere 4.2: 24 h / 15 - 20 °C View Scheme