Corey-winter synthesis, mechanism of the corey-chaykovsky reaction
Such ylides are able to transfer more than just a methylene group, and enantioselective induction can be observed if the ylide is chiral: Dimethyloxosulfonium methylide - known as the Corey-Chaykovsky Reagent - is a valuable alternative to dimethylsulfonium methylide and can be generated from trimethylsulfoxonium iodide. The ylide initially acts as a nucleophile toward the carbonyl compound.
Venkatram Reddy, Tetrahedron Lett.
Such syntheses can give very interesting results when expensive chiral sulfides are used for the synthesis of chiral epoxides. The resulting oxygen anion then reacts as an intramolecular nucleophile toward the now electrophilic ylide carbon, essays for death penalty debate bears a sulfonium cation as a good leaving group: A Novel Procedure for the Synthesis of Epoxides: Guanidine Bases in Synthesis: Synthesis of epoxides Corey-Chaykovsky Reaction The reaction of sulfur ylides with carbonyl compounds such as ketones or the related imines leads to the corresponding epoxides or aziridines.
Corey-Chaykovsky Epoxidation The reaction of sulfur ylides with enones gives cyclopropanes. Corey-Chaykovsky Cyclopropanation Mechanism of the Corey-Chaykovsky Reaction The ylides are generated in situ by the deprotonation of sulfonium halides with strong bases.
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