Practical Synthesis of α-Perfluoroalkyl Cyclic Imines and Amines

Abstract A convenient and simple approach for the preparation of α-CF 3 and α-C 2 F 5 substituted pyrrolines, tetrahydropyridines, tetrahydroazepine is described. Claisen condensation of N-protected cyclic amides with esters of perfluorocarboxylic acids followed by deprotection and decarboxylation i...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2010-01, Vol.2010 (1), p.120-126
Main Authors: Shevchenko, Nikolay E., Balenkova, Elisabeth S., Röschenthaler, Gerd-Volker, Nenajdenko, Valentine G.
Format: Article
Language:English
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Summary:Abstract A convenient and simple approach for the preparation of α-CF 3 and α-C 2 F 5 substituted pyrrolines, tetrahydropyridines, tetrahydroazepine is described. Claisen condensation of N-protected cyclic amides with esters of perfluorocarboxylic acids followed by deprotection and decarboxylation in acidic media leads to the desired products. Reduction of these imines permits to obtain 5-, 6-, and 7-membered cyclic amines with α-CF 3 or α-C 2 F 5 group in good to moderate overall yields.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0029-1217104