Efficient polymer-supported Sharpless alkene epoxidation catalyst

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Laetitia Canali, Jaana K. Karjalainen, David C. Sherrington and Osmo Hormi


Abstract

Linear poly(tartrate ester) ligands provide high chemical yields and enantiomeric excesses in the epoxidation of trans-hex-2-en-1-ol using Ti(OPri)4–tert-butyl hydroperoxide.


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