17413-48-8Relevant articles and documents
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Sawada,Inouye
, p. 2669,2670 (1969)
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Altmann,Erdmann
, p. 4891 (1970)
Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover
Phelan, James P.,Lang, Simon B.,Compton, Jordan S.,Kelly, Christopher B.,Dykstra, Ryan,Gutierrez, Osvaldo,Molander, Gary A.
supporting information, p. 8037 - 8047 (2018/07/03)
A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3-exo-tet ring closure, a pathway consistent with experimental and computational data.
Access to functionalized cyclopropylcarbinyl compounds from homoallylic ethers via zirconocene intermediates
Vasse, Jean-Luc,Szymoniak, Jan
, p. 6449 - 6451 (2007/10/03)
Cyclopropylcarbinylzirconium complexes were generated from homoallylic ethers and zirconocene (Cp2ZrCl2/2n-BuLi). They underwent further in situ transformations that is, bromination-substitution, transmetallation-functionalization and insertion reactions to afford various cyclopropylcarbinyl derivatives. In contrast, ring-opening products could be selectively obtained by treating the zirconium complex with MeLi, prior to functionalization.
