The Sharpless oxyamination (often known as Sharpless aminohydroxylation) is the
chemical reaction that converts an alkene to a vicinal
amino alcohol. The reaction is related to the
Sharpless dihydroxylation, which converts alkenes to vicinal diols. Vicinal amino-alcohols are important products in
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
and recurring
pharmacophores in
drug discovery
In the fields of medicine, biotechnology and pharmacology, drug discovery is the process by which new candidate medications are discovered.
Historically, drugs were discovered by identifying the active ingredient from traditional remedies or by ...
.
Mechanism
Akin to the dihydroxylation, the oxyamination involves the cycloaddition of the alkene to an imido Os(VIII) intermediate of the type OsO
3(NR). Such species are generated by treatment of
osmium tetroxide with the sodium chloramines. Typical procedures combine
chloramine-T
Chloramine-T is the organic compound with the formula CH3C6H4SO2NClNa. Both the anhydrous salt and its trihydrate are known. Both are white powders. Chloramine-T is used as a reagent in organic synthesis. It is commonly used as cyclizing agent in ...
, alkene, an osmium catalyst, and a chiral ligand. Related procedures use
benzyl carbamate (CbzNH
2), sodium hydroxide,
tert-butyl hypochlorite to give CbzNCl(Na).
:R
2NH + t-BuOCl → R
2NCl + t-BuOH
Further reading
Early papers in the development of this methodology.
*
Sharpless, K. B.; Patrick, D. W.; Truesdale, L. K.; Biller, S. A. ''
J. Am. Chem. Soc.'' 1975, ''97'', 2305. ()
*Herranz, E.; Biller, S. A.; Sharpless, K. B. ''
J. Am. Chem. Soc.'' 1978, ''100'', 3596-3598. ()
*Bäckvall, J. E.; Oshima, K.; Palermo, R. E.; Sharpless, K. B. ''
J. Org. Chem.'' 1979, ''44'', 1953. ()
References
{{Reflist
Organic redox reactions
Name reactions