Multi-step reaction with 8 steps
1.1: tetrahydrofuran / 4.5 h / -20 - 0 °C / Inert atmosphere
1.2: -10 °C / Saturated solution
2.1: L-Selectride / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere
4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 14 h / 20 - 40 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere
7.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 12.5 h / -78 - 20 °C / Inert atmosphere
8.1: hydrogenchloride / 1,4-dioxane / 2.83 h / 0 - 20 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; copper(l) iodide; tetrabutyl ammonium fluoride; L-Selectride; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane;
DOI:10.1016/j.bmc.2011.01.027