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Highly [beta]-Regioselective Friedel-Crafts Aminoalkylation of Pyrroles with Cyclic Perfluoroalkylated Imines

A Friedel-Crafts-type alkylation reaction was studied between various pyrroles and [alpha]-polyfluoroalkylated cyclic imines that were activated by Lewis acids. The reaction proceeded under mild conditions and provided a high yielding synthesis of [alpha]-CF3-substituted pyrrolidines and piperidines...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-05, Vol.2013 (15), p.3049
Main Authors: Shmatova, Olga I, Shevchenko, Nikolay E, Balenkova, Elisabeth S, Roschenthaler, Gerd-Volker, Nenajdenko, Valentine G
Format: Article
Language:English
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Summary:A Friedel-Crafts-type alkylation reaction was studied between various pyrroles and [alpha]-polyfluoroalkylated cyclic imines that were activated by Lewis acids. The reaction proceeded under mild conditions and provided a high yielding synthesis of [alpha]-CF3-substituted pyrrolidines and piperidines as well as seven-membered analogues that contained a pyrrole ring. The unpredictably high [beta]-selectivity for the aminoalkylation of both 1H-pyrrole and N-substituted pyrrole was observed as a result of a thermodynamically-controlled electrophilic substitution reaction. The computational data are in full agreement with the experimental results, which confirmed the observed regioselectivity as a result of the lower energy of the [beta]-substituted pyrroles that contain [alpha]-trifluoromethyl-substituted pyrrolidine, piperidine, and azepane rings. [PUBLICATION ABSTRACT]
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201201725