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Synthesis 2010(1): 120-126  
DOI: 10.1055/s-0029-1217104
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Practical Synthesis of α-Perfluoroalkyl Cyclic Imines and Amines

Nikolay E. Shevchenkoa, Elisabeth S. Balenkovaa, Gerd-Volker Röschenthaler*b, Valentine G. Nenajdenko*a
a Department of Chemistry, Moscow State University, Moscow 119991, Russian Federation
Fax: +7(495)9322286; e-Mail: nen@acylium.chem.msu.ru;
b Institute for Inorganic and Physical Chemistry, The University of Bremen, Leobener Str., 28334 Bremen, Germany
Fax: +38(421)2184267; e-Mail: gvr@chemie.uni-bremen.de;
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Publikationsverlauf

Received 20 August 2009
Publikationsdatum:
06. November 2009 (online)

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Abstract

A convenient and simple approach for the preparation of α-CF3 and α-C2F5 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-CF3 or α-C2F5 group in good to moderate overall yields.

Key words

fluorine - nitrogen heterocycles - α-polyfluoroalkyl imines­ - reductions

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11

A mixture of Claisen products 1a and 2a was isolated in this reaction.