Desymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7-exo-trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activity
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Issue Date
2018-04-26Author
Maslivetc, Vladimir A.
Turner, Danielle N.
McNair, Kimberly N.
Frolova, Liliyan
Rogelj, Snezna
Maslivetc, Anna C.
Aksenov, Nicolai A.
Rubina, Marina
Rubin, Michael
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
Copyright © 2018 American Chemical Society
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Show full item recordAbstract
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.
Description
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry,copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.8b00640
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Citation
Maslivetc, V. A., Turner, D. N., McNair, K. N., Frolova, L., Rogelj, S., Maslivetc, A. A., … Rubin, M. (2018). Desymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7- exo- trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activity. The Journal of organic chemistry, 83(10), 5650–5664. doi:10.1021/acs.joc.8b00640
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