Selective Synthesis of Functionalized Trifluoromethylated Pyrrolidines, Piperidines, and Azepanes Starting from 1‐Tosyl‐2‐(trifluoromethyl)aziridine | Zendy

Dolfen Jeroen | Zendy; Kenis Sara | Zendy; Van Hecke Kristof | Zendy; De Kimpe Norbert | Zendy; D'hooghe Matthias | Zendy

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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.

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