Arylcyclopropanes: Properties, Synthesis and Use in Medicinal Chemistry

Palladium‐Catalyzed Direct Cyclopropylation of Heterocycles

“…[31] Subsequent transmetalation of an anionic heterocycle and C À Cr eductive elimination leads to the coupling products.Thus,the pathway is different from that of our recent work on alkylation of common alkyl halides,areaction which relied on direct addition of alkyl radicals to the unsaturated rings. Thecoupling process is stereoretentive for the three-membered rings,and confirms that oxidative addition of cyclopropyl CÀXb onds to palladium(0) is ac oncerted process.…”

Highly Enantioselective Synthesis of 1,2,3‐Substituted Cyclopropanes by Using α‐Iodo‐ and α‐Chloromethylzinc Carbenoids

“…The cyclopropane unit continues to generate interest due to its unique bonding properties, its rigidity, and its numerous applications in diverse chemical transformations 1. This motif is present in several bioactive natural products as well as synthetic drugs, which has prompted the development of methodologies for their synthesis 2. The Simmons–Smith cyclopropanation reaction3 remains one of the most important methods for the formation of cyclopropane derivatives from alkenes 1e.…”

Catalytic C–H Bond Functionalization of Cyclopropane Derivatives

“…The prevalent methods employed include halomethylmetal mediated processes in the presence of chiral auxiliaries/catalysts (Simmons-Smith-type reactions), transition-metal-catalyzed decomposition of diazoalkanes, Michaelinduced ring closures, or asymmetric metalations [8][9][10]46]. However, the asymmetric preparation of unfunctionalized cyclopropanes remains relatively undisclosed.…”

“…Significant efforts have been dedicated to the syntheses of cyclopropanes in both racemic or enantioenriched forms [8][9][10]. Cyclopropanes may also act as precursors en route toward accessing more chemical complexity, via involvement in various reactions such as cycloadditions, ring openings, or cross-couplings.…”