RESUMO
This contribution describes the synthesis of several novel bicyclic α-amino endoperoxides, including CF(3)-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovich-de Meijere reaction), starting from N-alkenyl amides that contain a vic-disubstituted double bond, with high diastereoselectivity. An evaluation of the biological activities of several of the molecules produced, against the parasite Plasmodium falciparum, is also presented.
Assuntos
Aminas/química , Antimaláricos/síntese química , Ciclopropanos/síntese química , Peróxidos/química , Amidas/química , Cristalografia por Raios X , Ciclopropanos/farmacologia , Modelos Moleculares , Estrutura Molecular , Oxirredução , Plasmodium falciparum/efeitos dos fármacos , Relação Estrutura-AtividadeAssuntos
COVID-19 , Pandemias , França/epidemiologia , Humanos , Pandemias/prevenção & controle , SARS-CoV-2RESUMO
Keteniminium salts are powerful electrophilic heterocumulene reagents well-known for their selectivity and stereocontrol in [2+2] cycloadditions to olefins and carbonyl derivatives. Furthermore, they are readily accessible from stable and simple precursors under a variety of different conditions. Herein, we present the chemistry of keteniminium salts with the hindsight of time, describe preparation methods, recent [2+2] chemistry, mechanistic studies, and assorted applications that significantly extend the scope of utility of these unique electrophilic heterocumulenes.