American Chemical Society
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Diastereoselective Cascade Assembly of Functionalized Pyrano[3,4‑c]pyrrole Derivatives

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posted 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.