Back Dihydroxylierung German Hidroxilación de Upjohn Spanish Upjohn-dihydroxylering Dutch Di-hidrogenação de Upjohn Portuguese 厄普约翰双羟基化反应 Chinese
| Upjohn dihydroxylation | |
|---|---|
| Named after | The Upjohn Company |
| Reaction type | Addition reaction |
| Identifiers | |
| Organic Chemistry Portal | upjohn-dihydroxylation |
The Upjohn dihydroxylation is an organic reaction which converts an alkene to a cis vicinal diol. It was developed by V. VanRheenen, R. C. Kelly and D. Y. Cha of the Upjohn Company in 1976.[1] It is a catalytic system using N-methylmorpholine N-oxide (NMO) as stoichiometric re-oxidant for the osmium tetroxide. It is superior to previous catalytic methods.
Prior to this method, use of stoichiometric amounts of the toxic and expensive reagent osmium tetroxide was often necessary. The Upjohn dihydroxylation is still often used for the formation of cis-vicinal diols; however, it can be slow and is prone to ketone byproduct formation. One of the peculiarities of the dihydroxylation of olefins is that the standard "racemic" method (the Upjohn dihydroxylation) is slower and often lower yielding than the asymmetric method (the Sharpless asymmetric dihydroxylation).
- ^ Vanrheenen, V.; Kelly, R. C.; Cha, D. Y. (1976). "An improved catalytic OsO4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant". Tetrahedron Lett. 17 (23): 1973–1976. doi:10.1016/S0040-4039(00)78093-2.