1: With water; lithium hydroxide hydrate in tetrahydrofuran; methanol T=20°C; 2 h; 2: in tetrahydrofuran; methanol; water pH=2; Aqueous phosphate buffer; Product distribution / selectivity;

1: With lithium hydroxide hydrate in tetrahydrofuran; water T=15 - 20°C; 4.25 h; Inert atmosphere; 2: With hydrogenchloride in tetrahydrofuran; water pH=2.5 - 3.5; 2 h; Inert atmosphere;

water; lithium hydroxide hydrate in tetrahydrofuran; isopropyl alcohol

1.1: potassium tert-butylate / tetrahydrofuran / 2.33 h / 65 - 67 °C / Inert atmosphere 1.2: 3 h / 10 - 20 °C / Inert atmosphere 2.1: di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium / N,N-dimethyl-formamide / 7 h / 85 °C / Inert atmosphere 3.1: CDX-017 enzyme; pyridoxal 5'-phosphate / water; dimethyl sulfoxide / 52 h / 45 °C / pH 8.5 / Inert atmosphere; triethanolamine/isopropylamine buffer; Enzymatic reaction 3.2: 2 h / pH 6 / Inert atmosphere 4.1: sodium carbonate / isopropanol acetate; water / 0.08 h / 20 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 2.08 h / Inert atmosphere 6.1: lithium hydroxide hydrate / tetrahydrofuran; water / 4.25 h / 15 - 20 °C / Inert atmosphere 6.2: 2 h / pH 2.5 - 3.5 / Inert atmosphere View Scheme

1.1: toluene / 16 h / Reflux; Inert atmosphere 2.1: sulfuric acid / 2.5 h / 90 - 92 °C / Inert atmosphere 2.2: 5 - 18 °C / pH 7 / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 2.33 h / 65 - 67 °C / Inert atmosphere 3.2: 3 h / 10 - 20 °C / Inert atmosphere 4.1: di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium / N,N-dimethyl-formamide / 7 h / 85 °C / Inert atmosphere 5.1: CDX-017 enzyme; pyridoxal 5'-phosphate / water; dimethyl sulfoxide / 52 h / 45 °C / pH 8.5 / Inert atmosphere; triethanolamine/isopropylamine buffer; Enzymatic reaction 5.2: 2 h / pH 6 / Inert atmosphere 6.1: sodium carbonate / isopropanol acetate; water / 0.08 h / 20 °C / Inert atmosphere 6.2: 2 h / 20 °C / Inert atmosphere 7.1: potassium carbonate / N,N-dimethyl-formamide / 2.08 h / Inert atmosphere 8.1: lithium hydroxide hydrate / tetrahydrofuran; water / 4.25 h / 15 - 20 °C / Inert atmosphere 8.2: 2 h / pH 2.5 - 3.5 / Inert atmosphere View Scheme

1.1: sulfuric acid / 2.5 h / 90 - 92 °C / Inert atmosphere 1.2: 5 - 18 °C / pH 7 / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 2.33 h / 65 - 67 °C / Inert atmosphere 2.2: 3 h / 10 - 20 °C / Inert atmosphere 3.1: di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium / N,N-dimethyl-formamide / 7 h / 85 °C / Inert atmosphere 4.1: CDX-017 enzyme; pyridoxal 5'-phosphate / water; dimethyl sulfoxide / 52 h / 45 °C / pH 8.5 / Inert atmosphere; triethanolamine/isopropylamine buffer; Enzymatic reaction 4.2: 2 h / pH 6 / Inert atmosphere 5.1: sodium carbonate / isopropanol acetate; water / 0.08 h / 20 °C / Inert atmosphere 5.2: 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 2.08 h / Inert atmosphere 7.1: lithium hydroxide hydrate / tetrahydrofuran; water / 4.25 h / 15 - 20 °C / Inert atmosphere 7.2: 2 h / pH 2.5 - 3.5 / Inert atmosphere View Scheme

1.1: sodium tetrahydroborate / ethanol / 16 h / 0 °C / Inert atmosphere 2.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 1 h / Inert atmosphere 3.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 4.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 4.2: 1.67 h / Inert atmosphere 4.3: 1 h / Inert atmosphere 5.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C 6.2: 2 h / -60 - 20 °C 7.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere 8.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness 9.1: lithium hydroxide hydrate / tetrahydrofuran; water / 16.25 h / 20 °C / Inert atmosphere 9.2: 1 h / Inert atmosphere View Scheme

1.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 1 h / Inert atmosphere 2.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 3.2: 1.67 h / Inert atmosphere 3.3: 1 h / Inert atmosphere 4.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C 5.2: 2 h / -60 - 20 °C 6.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere 7.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness 8.1: lithium hydroxide hydrate / tetrahydrofuran; water / 16.25 h / 20 °C / Inert atmosphere 8.2: 1 h / Inert atmosphere View Scheme

1.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 2.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 2.2: 1.67 h / Inert atmosphere 2.3: 1 h / Inert atmosphere 3.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C 4.2: 2 h / -60 - 20 °C 5.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere 6.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness 7.1: lithium hydroxide hydrate / tetrahydrofuran; water / 16.25 h / 20 °C / Inert atmosphere 7.2: 1 h / Inert atmosphere View Scheme

1.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 1.2: 1.67 h / Inert atmosphere 1.3: 1 h / Inert atmosphere 2.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C 3.2: 2 h / -60 - 20 °C 4.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere 5.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness 6.1: lithium hydroxide hydrate / tetrahydrofuran; water / 16.25 h / 20 °C / Inert atmosphere 6.2: 1 h / Inert atmosphere View Scheme