Sharpless oxyamination
The Sharpless oxyamination (often known as Sharpless aminohydroxylation) is the
Sharpless dihydroxylation, which converts alkenes to vicinal diols.[1] Vicinal amino-alcohols are important products in organic synthesis and recurring pharmacophores in drug discovery
.
Mechanism
Akin to the dihydroxylation, the oxyamination involves the cycloaddition of the alkene to an imido Os(VIII) intermediate of the type OsO3(NR). Such species are generated by treatment of
tert-butyl hypochlorite to give CbzNCl(Na).[3]
- R2NH + t-BuOCl → R2NCl + t-BuOH
Further reading
Early papers in the development of this methodology.
- )
- Herranz, E.; Biller, S. A.; Sharpless, K. B. )
- Bäckvall, J. E.; Oshima, K.; Palermo, R. E.; Sharpless, K. B. )
References
- doi:10.1039/b111276g)
- doi:10.15227/orgsyn.061.0085.)
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