TheSharpless oxyamination (often known asSharpless aminohydroxylation) is thechemical reaction that converts analkene to a vicinalamino alcohol. The reaction is related to theSharpless dihydroxylation, which converts alkenes to vicinal diols.^[1] Vicinal amino-alcohols are important products inorganic synthesis and recurringpharmacophores indrug discovery.

Akin to the dihydroxylation, the oxyamination involves thecycloaddition of the alkene to an imido Os(VIII) intermediate of the type OsO₃(NR). Such species are generated by treatment ofosmium tetroxide with the sodium chloramines. Typical procedures combinechloramine-T, alkene, an osmium catalyst, and a chiral ligand.^[2] Related procedures usebenzyl carbamate (CbzNH₂),sodium hydroxide,tert-butyl hypochlorite to give CbzNCl(Na).^[3]

R₂NH + t-BuOCl → R₂NCl + t-BuOH

Early papers in the development of this methodology.

• Sharpless, K. Barry; Patrick, Donald W.; Truesdale, Larry K.; Biller, Scott A. (1975). "New reaction. Stereospecific vicinal oxyamination of olefins by alkyl imido osmium compounds".Journal of the American Chemical Society.97 (8):2305–2307.Bibcode:1975JAChS..97.2305S.doi:10.1021/ja00841a071.
• Herranz, Eugenio; Biller, Scott A.; Sharpless, K. Barry (1978). "Osmium-catalyzed vicinal oxyamination of olefins by N-chloro-N-argentocarbamates".Journal of the American Chemical Society.100 (11):3596–3598.Bibcode:1978JAChS.100.3596H.doi:10.1021/ja00479a051.
• Baeckvall, Jan E.; Oshima, Koichiro; Palermo, Robert E.; Sharpless, K. Barry (1979). "Some reactions of N-(2-hydroxyalkyl)-p-toluenesulfonamides and N-allyl-p-toluenesulfonamides".The Journal of Organic Chemistry.44 (12):1953–1957.doi:10.1021/jo01326a013.

• Organic redox reactions
• Name reactions

• CS1 maint: multiple names: authors list