Organic Chemistry

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12. Alcohols, Ethers, Epoxides and Thiols

Sharpless Epoxidation

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Epoxidation of an asymmetrical alkene is usually a non-stereospecfic process, yielding a racemic mixture of enantiomers. How do you select for one enantiomer over another?

 

Side note:K. Barry Sharpless figured this puzzle out in 1980, receiving a Nobel Prize in 2001. Go science!

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Important Reagents of Sharpless Epoxidation.

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Diethyl tartartes (DET) of different optical activities are used to convert allyl alcohols into stereospecific epoxides.  

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General reaction of Sharpless Epoxidation.

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How to draw and predict a Sharpless Epoxidation.

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Always draw alcohol on the bottom right corner of the double bond. Then determine which epoxide you get according to the DET used. 

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