1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere 1.2: 3 h / -40 - -10 °C / Inert atmosphere 2.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Reflux; Inert atmosphere 2.2: 6 h / -78 - -35 °C / Inert atmosphere 2.3: -35 °C / Inert atmosphere 3.1: hydrogenchloride; hydrogen; acetic acid / palladium 10 on activated carbon / water / 3 h / 20 °C / 760.05 Torr 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 24 h / 20 °C View Scheme

1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Reflux; Inert atmosphere 1.2: 6 h / -78 - -35 °C / Inert atmosphere 1.3: -35 °C / Inert atmosphere 2.1: hydrogenchloride; hydrogen; acetic acid / palladium 10 on activated carbon / water / 3 h / 20 °C / 760.05 Torr 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 24 h / 20 °C View Scheme

1: hydrogenchloride; hydrogen; acetic acid / palladium 10 on activated carbon / water / 3 h / 20 °C / 760.05 Torr 2: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 24 h / 20 °C View Scheme

1.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 2.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 3.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 4.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 5.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 5.2: 8 h / 50 °C / Reflux 6.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 7.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 7.2: Inert atmosphere View Scheme

1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 1.2: 2.25 h / -40 °C 2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux 3.1: hydrogen / palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 4.2: 20 °C / pH 3.5 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 5.2: 20 °C 6.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 7.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux 8.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 9.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 10.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 11.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 12.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 12.2: 8 h / 50 °C / Reflux 13.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 14.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 14.2: Inert atmosphere View Scheme

1.1: sodium tetrahydroborate; methanol 2.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 3.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux 4.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 5.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 6.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 7.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 8.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 8.2: 8 h / 50 °C / Reflux 9.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 10.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 10.2: Inert atmosphere View Scheme

1.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux 2.1: hydrogen / palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 3.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 3.2: 20 °C / pH 3.5 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 4.2: 20 °C 5.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 6.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux 7.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 8.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 9.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 10.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 11.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 11.2: 8 h / 50 °C / Reflux 12.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 13.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 13.2: Inert atmosphere View Scheme

1.1: hydrogen / palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 2.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 2.2: 20 °C / pH 3.5 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 3.2: 20 °C 4.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 5.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux 6.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 7.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 8.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 9.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 10.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 10.2: 8 h / 50 °C / Reflux 11.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 12.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 12.2: Inert atmosphere View Scheme

1.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 1.2: 20 °C / pH 3.5 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 2.2: 20 °C 3.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux 5.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 6.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 7.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 8.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 9.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 9.2: 8 h / 50 °C / Reflux 10.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 11.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 11.2: Inert atmosphere View Scheme

1.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 1.2: 20 °C / pH 3.5 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 2.2: 20 °C 3.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux 5.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 6.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 7.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 8.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 9.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 9.2: 8 h / 50 °C / Reflux 10.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 11.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 11.2: Inert atmosphere View Scheme