Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12258/385
Title: Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity
Authors: Aksenov, N. A.
Аксенов, Н. А.
Rubin, M. A.
Рубин, М. А.
Keywords: Desymmetrization of cyclopropenes
Issue Date: 2018
Publisher: American Chemical Society
Citation: Maslivetc, V.A., Turner, D.N., McNair, K.N., Frolova, L., Rogelj, S., Maslivetc, A.A., Aksenov, N.A., Rubina, M., Rubin, M. Desymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7- exo- trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activity // Journal of Organic Chemistry. - 2018. - Volume 83. - Issue 10. - pp. 5650-5664.
Series/Report no.: Journal of Organic Chemistry
Abstract: A strain-release-driven, cation-templated intramolecular nucleophilic addition of tethered alkoxides to prochiral cyclopropenes is described. Employment of chiral β- and γ-amino alkoxides allowed for highly diastereoselective assembly of a small series of enantiopure cyclopropane-fused oxazepanones. It was shown that the chiral center at C-4 plays a crucial role in controlling desymmetrization of the cyclopropenyl moiety, instigated by a profound potassium-templated effect. The preliminary biological activities of the new cyclopropane-fused medium heterocycles against Gram-positive bacteria, Gram-negative bacteria, mycobacteria, cancer cells, and fungus were evaluated
URI: https://www.scopus.com/record/display.uri?eid=2-s2.0-85047352177&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=nort*+caucas*+fed*+univ*&sid=ebf9446ddab8c0101772b7f698064ac5&sot=afnl&sdt=afsp&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=3&citeCnt=0&searchTerm=
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