Multi-step reaction with 10 steps
1.1: tetrahydrofuran / 0.5 h / -15 °C / Inert atmosphere
2.1: chloro([(S,2S)-(?)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido)(mesitylene)ruthenium (II); triethylamine; formic acid / 12 h / 20 °C / Inert atmosphere
3.1: potassium hydride; Trimethylenediamine / 18 h / 15 - 20 °C / Inert atmosphere
4.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
5.1: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere
5.2: 12 h / -20 - 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 14 h / 20 °C / Inert atmosphere
7.1: quinoline; 5% Pd-CaCO3; hydrogen / methanol / 18 h / 20 °C / 760.05 Torr / Inert atmosphere
8.1: bis(acetylacetonate)oxovanadium; tert.-butylhydroperoxide / dichloromethane; decane / 23 h / 0 - 20 °C / Inert atmosphere
9.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 15 h / 0 °C / Inert atmosphere
10.1: bis(tetrahydrofuran)-meso-tetra(4-chlorophenyl)porphyrinato aluminum tetracarbonyl cobaltate / tetrahydrofuran / 24 h / -30 - 50 °C / 46544.6 Torr / Autoclave; Inert atmosphere
With
1H-imidazole; quinoline; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; chloro([(S,2S)-(?)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido)(mesitylene)ruthenium (II); n-butyllithium; formic acid; bis(acetylacetonate)oxovanadium; di-isopropyl azodicarboxylate; 5% Pd-CaCO3; bis(tetrahydrofuran)-meso-tetra(4-chlorophenyl)porphyrinato aluminum tetracarbonyl cobaltate; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; Trimethylenediamine; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; decane; dichloromethane; N,N-dimethyl-formamide;
9.1: |Mitsunobu Displacement;
DOI:10.1021/ja505639u