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Synthesis of Chiral Piperazinones Using Amphoteric Aziridine Aldehyde Dimers and Functionalized Isocyanides
- Heine, Niklas
B., Kaldas, Sherif J., Belding, Lee, Shmatova, Olga, Dudding, Travis, Nenajdenko, Valentine G., Studer, Armido, Yudin, Andrei K.
- Journal of organic chemistry 2016 v.81 no.12 pp. 5209-5216
- aldehydes, ethyleneimine, organic chemistry
- We have evaluated a range of functionalized isocyanides in the aziridine aldehyde-driven multicomponent synthesis of piperazinones. High diasteroselectivity for each isocyanide was observed. A theoretical evaluation of the reaction course corroborates the experimental data. Moreover, the reactivity of cis- and trans-configured aziridine aldehyde dimers has been compared. This study further probes the dimer-driven mechanism of cyclization and enables an efficient access to a wide range of chiral piperazinones bearing functionalized side chains.