Why is the Sharpless epoxidation enantioselective?
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Sharpless epoxidation. The Sharpless epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols. ... Enantioselectivity is achieved by a catalyst formed from titanium tetra(isopropoxide) and diethyl tartrate.
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Sharpless epoxidation is enantioselective because if we see the mechanism of epoxidation, we find that oxidant in the reaction is tert-butyl hydroperoxide which is catalysed by Ti(O/Pr)4. This catalyst acts as a binding agent for hyderoperoxide, allylic alcohol group and tartrate. And so epoxidation of prochiral allylic alcohol is enantioselective(Depend upon the catalyst only one enantiomer is produced).
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