Abstract
Abstract The synthesis of monosubstituted or geminally disubstituted epoxides from aldehydes or ketones with either methylsulfonium or methyloxosulfonium ylides is referred to as the Corey–Chaykovsky reaction. The methylsulfonium or methyloxosulfonium ylide is known as the Corey–Chaykovsky reagent. The mechanisms for the preparation of trimethylsulfoxonium ylide (Me 2 S=CH 2 ) have been explained and it has been found that the ylide behaves as a nucleophile at the initial stage, and epoxide is formed from a backside attack of an oxido anion on the β‐carbon. The pentacoordinate 1,2γ‐oxathietanes are reported to be the intermediates in the addition step of this reaction. A few mechanisms have been proposed for this epoxidation. So far, different chiral sulfur ylides have been designed as shown in reaction scheme.
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