Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic framework

Iodine radical mediated cascade [3 + 2] carbocyclization of ene-vinylidenecyclopropanes with thiols and selenols via photoredox catalysis

“…9 e In our previous paper, we have described that some unknown side reaction products could be formed upon photoirradiation of ethyl iododifluoroacetate. 16…”

Stereoconvergent Direct Ring Expansion of Cyclopropyl Ketones to Cyclopentanones

“…While traditional approaches like the Nazarov, Pauson–Khand, and Karpf–Dreiding reactions have provided access to the pentacyclic framework, more efficient methods for structurally diverse cyclopentanones remains highly desirable . A formal allylic transposition of the cyclopropyl C–C bond of vinylcyclopropanes, i.e., vinylcyclopropane–cyclopentene (VCP) rearrangement, provides a powerful pentannulation method. VCP rearrangement of vinylcyclopropanes oxygenated at the vinyl ( 1 ) or cyclopropyl ( 2 ) groups gives cyclopentenyl ethers 3 , which are converted to cyclopentanones 4 by hydrolysis (Scheme , a left).…”

Tetrahedron looking back, Tetrahedron Chem looking forward

“…Catalysis is well represented, as Liu-Zhu Gong and co-workers report a modular route to chiral cyclopentanes by palladium and chiral squaramide relay catalysis [9]. A full paper from the team of Feng Shi reports the organocatalytic asymmetric synthesis of indoline-connected allenes bearing multiple chiral elements in a single step [10], and photocatalysis is showcased in a paper from Min Shi, Yin Wei and Zhen Liu, on a photocatalytic interrupted Cloke-Wilson rearrangement for the synthesis of oxy-bridged macrocycles [11]. Synthetic supramolecular chemistry is highlighted with a report from Qing He and team describing a facile and efficient synthetic approach to emissive superphanes with unique host-guest binding properties [12].…”