18448-15-2Relevant academic research and scientific papers
Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate
Sekiguchi, Yoshiya,Lee, Yan Ying,Yoshikai, Naohiko
supporting information, p. 5993 - 5997 (2021/08/16)
We report herein a nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates that occurs under mild and neutral conditions. The reaction displays linear selectivity for both linear and branched acyclic allylic carbonates and is also applicable to cyclic allylic carbonates, affording a variety of δ,?-unsaturated ketones in moderate to good yields. Mechanistic experiments are in accord with a catalytic cycle involving decarboxylative oxidative addition of allylic carbonate to Ni(0), alkoxide exchange with cyclopropanol, cyclopropoxide-to-homoenolate conversion on Ni(II), and C-C reductive elimination.
Formation of polycyclic lactones through a ruthenium-catalyzed ring-closing metathesis/hetero-pauson-khand reaction sequence
Finnegan, David F.,Snapper, Marc L.
, p. 3644 - 3653 (2011/06/24)
Processes that form multiple carbon-carbon bonds in one operation can generate molecular complexity quickly and therefore be used to shorten syntheses of desirable molecules. We selected the hetero-Pauson-Khand (HPK) cycloaddition and ring-closing metathe
Stereo- and regioselectivity of cyclization reactions in conformationally restricted epoxy ketones: Evaluation of C- versus O-alkylation process
Crotti, Paolo,Badalassi, Fabrizio,Di Bussolo, Valeria,Favero, Lucilla,Pineschi, Mauro
, p. 8559 - 8572 (2007/10/03)
The intramolecular addition reaction of metal enolates of ketones to oxiranes has been applied to a series of epoxy ketones derived from cyclohexene oxide. γ-Hydroxy ketones (γ-HKs, C-alkylation products) or hydroxy enol ethers (HEEs, O-alkylation products) are obtained, depending on the nature of the cyclic transition state in each case involved and the application of the Fu?rst-Plattner rule. The formation of HEEs by reaction of the same epoxy ketones under acid conditions is also described. In some cases, regioconvergent or chemoselective processes are conveniently obtained.
