Sharpless epoxidation
| Sharpless epoxidation | |
|---|---|
| Named after | Karl Barry Sharpless |
| Reaction type | Ring forming reaction |
| Identifiers | |
| Organic Chemistry Portal | sharpless-epoxidation |
| RSC ontology ID | RXNO:0000141 |
The Sharpless epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols. The oxidizing agent is tert-butyl hydroperoxide. The method relies on a catalyst formed from titanium tetra(isopropoxide) and diethyl tartrate.
2,3-Epoxyalcohols can be converted into diols, aminoalcohols, and ethers. The reactants for the Sharpless epoxidation are commercially available and relatively inexpensive. K. Barry Sharpless published a paper on the reaction in 1980 and was awarded the 2001 Nobel Prize in Chemistry for this and related work on asymmetric oxidations. The prize was shared with William S. Knowles and Ryōji Noyori.
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