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Selective Synthesis of Functionalized Trifluoromethylated Pyrrolidines, Piperidines, and Azepanes Starting from 1‐Tosyl‐2‐(trifluoromethyl)aziridine
Author(s) -
Dolfen Jeroen,
Kenis Sara,
Van Hecke Kristof,
De Kimpe Norbert,
D'hooghe Matthias
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304759
Subject(s) - trifluoromethyl , tosyl , aziridine , chemistry , nucleophile , ring (chemistry) , halogen , alkylation , organic chemistry , fluorine , sulfur , combinatorial chemistry , medicinal chemistry , catalysis , alkyl
This paper reports on the generation and alkylation of the 1‐tosyl‐2‐(trifluoromethyl)aziridin‐2‐yl anion with ω,ω′‐dihaloalkanes, followed by a novel ring‐expansion protocol toward 2‐CF 3 ‐pyrrolidines, 2‐CF 3 ‐piperidines, and 3‐CF 3 ‐azepanes. A variety of halogen, oxygen, nitrogen, sulfur, and carbon nucleophiles was used to trigger this ring rearrangement, resulting in CF 3 ‐azaheterocycles bearing different types of functionalized side chains.