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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
Maslivetc, Vladimir A. Turner, Danielle N. McNair, Kimberly N. Frolova, Liliyan Rogelj, Snezna Maslivetc, Anna C. Aksenov, Nicolai A. Rubina, Marina Rubin, Michael
Maslivetc, Vladimir A.
Turner, Danielle N.
McNair, Kimberly N.
Frolova, Liliyan
Rogelj, Snezna
Maslivetc, Anna C.
Aksenov, Nicolai A.
Rubina, Marina
Rubin, Michael
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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.
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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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2018-04-26
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American Chemical Society
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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