posted on 2016-04-06, 12:47authored byMikhail 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.