Dimethyloxosulfonium methylide

Johnson–Corey–Chaykovsky reaction
Named after	A. William Johnson Elias James Corey Michael Chaykovsky
Reaction type	Ring forming reaction
Identifiers
Organic Chemistry Portal	corey-chaykovsky-reaction

The Johnson–Corey–Chaykovsky reaction (sometimes referred to as the Corey–Chaykovsky reaction or CCR) is a chemical reaction used in organic chemistry for the synthesis of epoxides, aziridines, and cyclopropanes. It was discovered in 1961 by A. William Johnson and developed significantly by E. J. Corey and Michael Chaykovsky. The reaction involves addition of a sulfur ylide to a ketone, aldehyde, imine, or enone to produce the corresponding 3-membered ring. The reaction is diastereoselective favoring trans substitution in the product regardless of the initial stereochemistry. The synthesis of epoxides via this method serves as an important retrosynthetic alternative to the traditional epoxidation reactions of olefins.

The reaction is most often employed for epoxidation via methylene transfer, and to this end has been used in several notable total syntheses (See Synthesis of epoxides below). Additionally detailed below are the history, mechanism, scope, and enantioselective variants of the reaction. Several reviews have been published.

The original publication by Johnson concerned the reaction of 9-dimethylsulfonium fluorenylide with substituted benzaldehyde derivatives. The attempted Wittig-like reaction failed and a benzalfluorene oxide was obtained instead, noting that "Reaction between the sulfur ylid and benzaldehydes did not afford benzalfluorenes as had the phosphorus and arsenic ylids."

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