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Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity

Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity

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....

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Главные авторы: Aksenov, N. A., Аксенов, Н. А., Rubin, M. A., Рубин, М. А.
Формат: Статья
Язык:English
Опубликовано: American Chemical Society 2018
Темы:
Desymmetrization of cyclopropenes
Online-ссылка:https://dspace.ncfu.ru:443/handle/20.500.12258/385
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spelling ir-20.500.12258-3852025-02-13T09:30:02Z Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity Aksenov, N. A. Аксенов, Н. А. Rubin, M. A. Рубин, М. А. Desymmetrization of cyclopropenes 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 2018-05-31T14:23:50Z 2018-05-31T14:23:50Z 2018 Статья 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. https://dspace.ncfu.ru:443/handle/20.500.12258/385 en Journal of Organic Chemistry application/pdf application/pdf American Chemical Society
institution СКФУ
collection Репозиторий
language English
topic Desymmetrization of cyclopropenes
spellingShingle Desymmetrization of cyclopropenes
Aksenov, N. A.
Аксенов, Н. А.
Rubin, M. A.
Рубин, М. А.
Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity
description 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
format Статья
author Aksenov, N. A.
Аксенов, Н. А.
Rubin, M. A.
Рубин, М. А.
author_facet Aksenov, N. A.
Аксенов, Н. А.
Rubin, M. A.
Рубин, М. А.
author_sort Aksenov, N. A.
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
title_short Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity
title_full Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity
title_fullStr Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity
title_full_unstemmed Desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity
title_sort desymmetrization of cyclopropenes via the potassium-templated diastereoselective 7- exo- trig cycloaddition of tethered amino alcohols toward enantiopure cyclopropane-fused oxazepanones with antimycobacterial activity
publisher American Chemical Society
publishDate 2018
url https://dspace.ncfu.ru:443/handle/20.500.12258/385
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