Multi-step reaction with 11 steps
1.1: sodium hydride / nujol; tetrahydrofuran / 16.5 h / 0 °C
1.2: 3.3 h / 0 °C
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux
3.1: (R)-Tol-BINAP; tetrabutylammonium triphenyldifluorosilicate; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran / 16 h / -78 °C
4.1: methanol; toluene / 1 h / 110 °C / Sealed tube
5.1: potassium carbonate / acetone / 5 h
6.1: hydrogen / isopropyl alcohol / 6 h / 20 °C
7.1: trimethylaluminum / toluene; dichloromethane / 0.58 h / 0 °C
7.2: 1.17 h / 0 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C
9.1: triethylamine; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper(l) iodide; triphenylphosphine / N,N-dimethyl-formamide / 9 h / 60 °C
10.1: chloro {[(1S,2S)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(mesitylene)ruthenium(II); sodium formate; 1-butyl-3-methylimidazolium Tetrafluoroborate / ethyl acetate; water / 7 h / 20 °C
11.1: tetrakis(triphenylphosphine) palladium(0); tri-n-butyl-tin hydride / hexane / 1 h
11.2: 1 h / -78 °C
11.3: -78 - 20 °C
With
2,6-dimethylpyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); chloro {[(1S,2S)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(mesitylene)ruthenium(II); palladium bis[bis(diphenylphosphino)ferrocene] dichloride; (R)-Tol-BINAP; hydrogen; trimethylaluminum; tri-n-butyl-tin hydride; sodium formate; copper(II) bis(trifluoromethanesulfonate); sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; tetrabutylammonium triphenyldifluorosilicate; 1-butyl-3-methylimidazolium Tetrafluoroborate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; nujol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene;
3.1: |Mukaiyama Aldol Addition / 10.1: |Noyori Asymmetric Hydrogenation;
DOI:10.1039/c3ob27508f