CoreyChaykovskytype

CoreyChaykovskytype refers to a family of sulfur ylide–mediated transformations in organic synthesis that modify carbonyl compounds to give either epoxides or alkenes. Named after Elias James Corey and Vladimir Chaykovsky, these reactions employ sulfonium or sulfoxonium ylides generated in situ and used to transfer a one-carbon unit to carbonyl substrates under relatively mild conditions. The approach has become a versatile tool in synthetic chemistry, complementing other carbonyl olefination and epoxidation methods.

The core reagents are sulfonium or sulfoxonium salts, such as trimethylsulfoxonium salts or related sulfonium derivatives. These ylides are typically generated by deprotonation with a strong base (for example, sodium hydride, potassium tert-butoxide, or sodium amide) in polar aprotic solvents. The ylide adds to aldehydes or ketones to form a sulfur-containing intermediate that collapses to the desired product. Depending on the reaction setup, the process can furnish methylenated alkenes (methylenation) or epoxides, providing two complementary pathways from the same class of reagents.

Substrates are mainly carbonyl compounds, including formaldehyde, aliphatic and aromatic aldehydes, and many ketones. The method generally tolerates a range of functional groups, though sterically hindered carbonyls or functionalities sensitive to strong bases may require adjusted conditions. The Corey-Chaykovsky type reactions are valued for their operational simplicity, mildness, and compatibility with diverse functional groups, making them useful in natural product synthesis and complex molecule construction.

See also: Corey–Chaykovsky reaction, Chaykovsky reaction.