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Sharpless Asymmetric Epoxidation

Sharpless asymmetric oxidation
  Named Reactions in Organic Synthesis
Reaction category:
Oxidation

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In 1980 K.B. Sharpless and T. Katsuki discovered that the combination of titanium (IV) tetraisopropoxide, optically active diethyl tartrate and tert-butyl hydroperoxide caused a wide variety of allylic alcohols to epoxidize in high yields. Hence forward the titanium (IV) alkoxide-catalyzed epoxidation of prochiral and chiral allylic alcohols in the presence of a chiral tartrate ester and an alkyl hydroperoxide to provide enantiopure 2,3-epoxy alcohols is known as the Sharpless asymmetric epoxidation (SAE).

Only allylic alcohols are good substrates for this method as the presence of a hydroxyl group is essential. The addition of catalytic amounts of molecular sieves allows for the use of only catalytic amounts of the titanium–tartrate complex, whereas without the molecular sieves a full equivalent of the complex is required.




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Some relevant Alfa Aesar products for the Sharpless asymmetric epoxidation:

Titanium(IV) isopropoxide, 99.995% (metals basis)
Titanium(IV) isopropoxide, 95%
Titanium(IV) isopropoxide, 97+%
(-)-Diethyl D-tartrate, 99%


We have a number of allylic alcohols substrates.

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