Sharpless Oxyamination

K. B. Sharpless et al., J. Am. Chem. Soc. 97, 2305 (1975).

-mediated cis-addition of nitrogen and oxygen moieties to mono-, di- and tri-substituted olefins to yield vicinal amino or amido alcohols:



Methods development in the context of taxol synthesis: L. Mangatal et al., Tetrahedron 45, 4177 (1989). Synthetic applications: S. K. Dubey, E. E. Knaus, Can. J. Chem. 61, 565 (1983); M. Lemaire et al., Synlett 1990, 615. Brief review: Organic Syntheses by Oxidation with Metal Compounds, W. J. Mijs, C. R. H. I. de Jonge, Eds. (Plenum Press, New York, 1986) pp 642-645.