Multi-step reaction with 9 steps
1.1: acetic acid; zinc / ethanol / 12 h / 20 °C
2.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0 - 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux; Inert atmosphere
4.1: 1H-imidazole / dichloromethane / 0.17 h / 0 °C
4.2: 6 h / 0 - 20 °C
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 - 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3 h / 20 °C
7.1: (S)-[1,1']-binaphthalenyl-2,2'-diol; titanium(IV)isopropoxide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve
7.2: 24 h / -78 - -20 °C / Inert atmosphere; Molecular sieve
8.1: dmap / 1 h / 0 - 20 °C / Inert atmosphere
9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; lithium aluminium tetrahydride; (S)-[1,1']-binaphthalenyl-2,2'-diol; titanium(IV)isopropoxide; di(n-butyl)tin oxide; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2014.04.026