Dichloromethane → (S)-2-methylpropane-2-sulfinamide tert-butyl(dimethyl){[(1S,2R,5E)-2-methyl-6-(4-nitrophenyl)-1-(phenoxymethyl)hex-5-en-1-yl]oxy}silane

Participants

Reaction Conditions

Reaction Steps

The major product alkene, N-[(1R)-1-((1S)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-phenoxyethyl)pent-4-en-1-yl]-2-methylpropane-2-sulfinamide (160 mg; 0.364 mmol) from Step F, 4-nitrostyrene (220 mg; 1.475 mmol) and Grubbs-II metathesis catalyst (45 mg; 0.053 mmol) were combined in anhydrous methylene chloride (6 ml) and the resulting reaction mixture stirred for 20 hours at 35° C. The crude product solution was concentrated under reduced pressure and the residues purified by silica gel plate chromatography on (20 cm×20 cm×1000 microns) eluted with hexanes and ethyl acetate (2:1 v/v) from which 116 mg of the desired metathesis product was obtained, m/z (ES) 561.22 (M+H)+.

Provenance & Evidence