Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo-trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates

• DOI: 10.1021/acs.joc.8b02062
• Publication Date: 2018-10-24T18:58:27Z
• Authors: Vladimir A. Masli...; Liliya V. Frolova; Snezna Rogelj; Anna A. Maslivetc; Marina Rubina; Michael Rubin
• Keywords: Cyclopropane; Nucleophilic Addition

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- regioselective fashion allows for preparation the corresponding 2,5-diazabicyclo[5.1.0]octan-6-ones 2,6-diazabicyclo[6.1.0]nonan-7-ones as sole products high yields. Preliminary studies on anticancer activities these novel cyclopropane-fused medium heterocycles were performed.