Multi-step reaction with 9 steps
1.1: lithium chloride / water / 21 °C / Schlenk technique
2.1: copper(I) bromide dimethylsulfide complex / diethyl ether; tert-butyl methyl ether / 0.17 h / -78 °C / Schlenk technique
2.2: 19 h / Schlenk technique
3.1: diisobutylaluminium hydride / dichloromethane / 2 h / Schlenk technique; Cooling with ethanol-dry ice
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 21 °C / Schlenk technique
4.2: 3 h / Schlenk technique
5.1: hydrazine hydrate; riboflavin / 24 h / 21 °C / Inert atmosphere; Schlenk technique
6.1: [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II) / diethyl ether / 0.25 h / 21 °C / Inert atmosphere; Schlenk technique
6.2: 0.08 h / Inert atmosphere; Schlenk technique
6.3: 16 h / Inert atmosphere; Schlenk technique
7.1: dicyclohexyl-carbodiimide; dmap / n-heptane / 16 h / 0 °C / Schlenk technique
8.1: acetonitrile boron trifluoride complex / dichloromethane / 0.08 h / 21 °C / Schlenk technique
9.1: 4,5-dicyano-1H-imidazole / dichloromethane / 0 °C / Schlenk technique
9.2: -20 °C / Schlenk technique
With
dmap; 4,5-dicyano-1H-imidazole; [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); copper(I) bromide dimethylsulfide complex; acetonitrile boron trifluoride complex; diisobutylaluminium hydride; hydrazine hydrate; dicyclohexyl-carbodiimide; lithium chloride; lithium hexamethyldisilazane; riboflavin;
In
tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; tert-butyl methyl ether; water;
1.1: |Wittig Olefination / 4.2: |Wittig Olefination;
DOI:10.1039/c3ob41483c