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Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo-trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates
Maslivetc, Vladimir A. Frolova, Liliya V. Rogelj, Snezna Maslivetc, Anna A. Rubina, Marina Rubin, Michael
Maslivetc, Vladimir A.
Frolova, Liliya V.
Rogelj, Snezna
Maslivetc, Anna A.
Rubina, Marina
Rubin, Michael
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Abstract
A strain-release-driven, cation-templated nucleophilic 7- and 8-exo-trig-cyclization of tethered Boc-protected amines to cyclopropenes is described. The featured reaction proceeds in diastereo- and regioselective fashion and allows for preparation of the corresponding 2,5-diazabicyclo[5.1.0]octan-6-ones and 2,6-diazabicyclo[6.1.0]nonan-7-ones as sole products in high yields. Preliminary studies on anticancer activities of these novel cyclopropane-fused medium heterocycles were performed.
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This document is the Accepted Manuscript version of a Published Work that appeared in final form in The 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 http://doi.org/10.1021/acs.joc.8b02062.
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2018-10-24
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American Chemical Society
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Maslivetc, V. A., Frolova, L. V., Rogelj, S., Maslivetc, A. A., Rubina, M., & Rubin, M. (2018). Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates. The Journal of organic chemistry, 83(22), 13743–13753. doi:10.1021/acs.joc.8b02062