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Nucleophilic epoxidation is the formation of epoxides from electron-deficient double bonds through the action of nucleophilic oxidants. Nucleophilic epoxidation methods represent a viable alternative to electrophilic methods, many of which do not epoxidize electron-poor double bonds efficiently. (1) Asymmetric versions of the above reaction have taken advantage of a number of strategies for achieving asymmetric induction. The highest yielding and most enantioselective methods include:

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  • Nucleophilic epoxidation is the formation of epoxides from electron-deficient double bonds through the action of nucleophilic oxidants. Nucleophilic epoxidation methods represent a viable alternative to electrophilic methods, many of which do not epoxidize electron-poor double bonds efficiently. Although the most commonly used asymmetric epoxidation methods (the Sharpless-Katsuki, and Jacobsen epoxidations) rely on the catalytic reactivity of electrophilic oxidants, nucleophilic oxygen sources substituted with a suitable leaving group can also act as epoxidation reagents. The classic example, the Weitz-Scheffer reaction employs hydrogen peroxide under basic conditions (Z = OH below). Other notable examples have employed hypochlorites (Z = Cl) and chiral peroxides (Z = OR*). (1) Asymmetric versions of the above reaction have taken advantage of a number of strategies for achieving asymmetric induction. The highest yielding and most enantioselective methods include: * Use of stoichiometric chiral oxidant * Use of stoichiometric metal peroxides substituted with chiral ligands * Use of stoichiometric chiral base * Use of polypeptides Although the mechanisms of each of these reactions differ somewhat, in each case the chiral catalyst or reagent must be involved in the enantio determining conjugate addition step. Cis-epoxides are difficult to access using nucleophilic epoxidation methods. Nearly all nucleophilic epoxidations of cis olefins afford trans epoxides. (en)
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  • Nucleophilic epoxidation is the formation of epoxides from electron-deficient double bonds through the action of nucleophilic oxidants. Nucleophilic epoxidation methods represent a viable alternative to electrophilic methods, many of which do not epoxidize electron-poor double bonds efficiently. (1) Asymmetric versions of the above reaction have taken advantage of a number of strategies for achieving asymmetric induction. The highest yielding and most enantioselective methods include: (en)
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  • Asymmetric nucleophilic epoxidation (en)
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