Tris(furan-2-yl)phosphane → (5R)-3-{4'-[5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]-4,5-dihydroisoxazole (0.5 g, 1.1 mmol), (5R)-3-(4-iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (0.49 g, 1.32 mmol), and tri-2-furylphosphine (0.051 g, 0.22 mmol) were dissolved in 1,4-dioxane (6 ml) and degassed three times. Tris (dibenzylideneacetone)palladium (0) (0.1 g, 0.11 mmol) was added and the solution was degassed three times. The solution was stirred and heated to 90° C. for 18 hours. The mixture was concentrated in vacuo and then purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent giving 0.24 g desired product.

Provenance & Evidence