Diastereoselective Cascade Assembly of Functionalized Pyrano[3,4‑c]pyrrole Derivatives
datasetposted on 2016-04-06, 12:47 authored by Mikhail Yu. Ievlev, Oleg V. Ershov, Viktor A. Tafeenko
A novel convenient approach for the synthesis of densely functionalized pyrano[3,4-c]pyrrole derivatives was developed. Cascade transformation of the simple adducts of tetracyanoethylene (TCNE) and ketones (4-oxoalkane-1,1,2,2-tetracarbonitriles) in the presence of aldehyde under the action of acetic acid led to the diastereoselective formation of targeted pyrano[3,4-c]pyrroles. The reaction pathway was thoroughly investigated, and proposed intermediates were shown to be consistent with experiment.