Sharpless epoxidation

The Sharpless epoxidation reaction is an <a href="/facts/Enantiomer/wjPv5J3y">enantioselective</a> <a href="/facts/Chemical_reaction/GpqWlKrz">chemical reaction</a> to prepare 2,3-epoxyalcohols from primary and secondary <a href="/facts/Allyl_alcohol/6HW6IS5U">allylic alcohols</a>. The <a href="/facts/Oxidizing_agent/1FQzB8pQ">oxidizing agent</a> is <a href="/facts/Tert-Butyl_hydroperoxide/kDNH7oSM">tert-butyl hydroperoxide</a>. The method relies on a <a href="/facts/Catalyst/LPBS7TQC">catalyst</a> formed from <a href="/facts/Titanium_isopropoxide/QjnVqFse">titanium tetra(isopropoxide)</a> and <a href="/facts/Diethyl_tartrate/VqlXmHrx">diethyl tartrate</a>.

2,3-Epoxyalcohols can be converted into <a href="/facts/Diol/pmaVtfKx">diols</a>, aminoalcohols, and <a href="/facts/Ether/jwDg0IKr">ethers</a>. The reactants for the Sharpless epoxidation are commercially available and relatively inexpensive.
<a href="/facts/K._Barry_Sharpless/yV32KFUn">K. Barry Sharpless</a> published a paper on the reaction in 1980 and was awarded the <a href="/facts/2001_Nobel_Prize_in_Chemistry/8Nb8Ajjy">2001 Nobel Prize in Chemistry</a> for this and related work on asymmetric <a href="/facts/Oxidations/Pyd5RVcj">oxidations</a>. The prize was shared with <a href="/facts/William_S._Knowles/KIIqB7h5">William S. Knowles</a> and <a href="/facts/Ry%C5%8Dji_Noyori/Hm23tw5X">Ryōji Noyori</a>.

Sharpless epoxidation open-in-new

Sharpless epoxidation