PubAg

Main content area

Synthesis of Chiral Piperazinones Using Amphoteric Aziridine Aldehyde Dimers and Functionalized Isocyanides

Author:
Heine, Niklas B., Kaldas, Sherif J., Belding, Lee, Shmatova, Olga, Dudding, Travis, Nenajdenko, Valentine G., Studer, Armido, Yudin, Andrei K.
Source:
Journal of organic chemistry 2016 v.81 no.12 pp. 5209-5216
ISSN:
1520-6904
Subject:
aldehydes, ethyleneimine, organic chemistry
Abstract:
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.
Agid:
5505563