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Published TCIMAIL newest issue No.198
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Sharpless-Katsuki Asymmetric Epoxidation
Sharpless-Katsuki asymmetric epoxidation is a reaction to convert allyl alcohols to optically active epoxyalcohols. In this reaction, asymmetric epoxyalcohols are generated from allyl alcohols by the treatment of titanium(IV) isopropoxide, tartrate diester, TBHP and molecular sieves in high yields and high enantioselectivities. This reaction has a substrate versatility and can afford asymmetric epoxyalcohols. Furthermore, one of its advantages is that the stereochemistry of the product can be easily anticipated from the used tartrate diester. In addition, it is effective for the optical resolution of racemic secondary allyl alcohols since one enantiomer is epoxidized prior to the other enantiomer, which makes it possible to separate them with high enantioselectivity.
Sharpless won the Nobel Prize for Chemistry in 2001 for the development of stereoselective oxidations including this reaction.
- Reagents:
- TBHP, Ti(OiPr)4, Tartrate diesters
- Reactants:
- Allyl alcohols
- Products:
- Asymmetric epoxyalcohols
- Scheme:
-
- Original literature:
-
- The first practical method for asymmetric epoxidation
- Asymmetric epoxidation provides shortest routes to four chiral epoxy alcohols which are key intermediates in syntheses of methymycin, erythromycin, leukotriene C-1, and disparlure
- Review literature:
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- Asymmetric Epoxidation of Allylic Alcohols: The Sharpless Epoxidation
- Applications of Sharpless asymmetric epoxidation in total synthesis
