Sulfur ylides enable a stereoelectronically-assisted C–C bond insertion followed by Corey–Chaykovsky cyclopropanation or epoxidation, allowing for dual CH2 transfer to alkenes and aldehydes.
This study presents the first interrupted Corey–Chaykovsky reaction of α,β-ynones, uncovering a novel mechanistic feature and enabling the synthesis of unprecedented polycyclic architectures.
Operationally straightforward substrate-based cyclization pathways facilitated by dimethyloxosulfonium methylide on designed enone-tethered azaarenium salts provide access to unprecedented classes of cyclopropanoids.
2-Indolyl-derived donor–acceptor cyclopropanes were smoothly converted into 4-substituted carbazoles via a cascade of Friedel–Crafts annulation and ring expansion triggered by HCl in different media.
A new synthetic method for terminal olefins was developed through the reaction of the Corey–Chaykovsky reagent with readily available esters. A mechanism involving nucleophilic addition, elimination and rearrangement is supported by DFT calculations.