Synthesis of 2‐Fluoroalkyl 4‐Substituted Azepanes

Synthesis of di‐ and tri‐substituted fluoroalkylated azepanes was achieved by ring expansion of pyrrolidines via a regioselective attack of nucleophiles on a bicyclic azetidinium intermediate. A broad scope of azepanes, substituted at C4 and bearing a α‐trifluoromethyl, α‐difluoromethyl or α‐perfluo...

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Published inEuropean journal of organic chemistry Vol. 2019; no. 31-32; pp. 5497 - 5507
Main Authors Masson, Guillaume, Rioton, Sarah, Gomez Pardo, Domingo, Cossy, Janine
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.09.2019
Wiley Subscription Services, Inc
Wiley-VCH Verlag
SeriesHeterocyclic Chemistry
Subjects
Azepanes
Azetidinium
Chemical Sciences
Chemistry
Chemistry, Organic
Fluoroalkyl groups
Nucleophiles
Organic chemistry
Physical Sciences
Regioselectivity
Ring expansion
Ring opening
Science & Technology
Substitutes
Synthesis
REARRANGEMENT
Regioselectivity
ANALOGS
Fluoroalkyl groups
Azepanes
FLUORINE
PROLINOLS
Azetidinium
Ring opening
Ring expansion
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Summary:Synthesis of di‐ and tri‐substituted fluoroalkylated azepanes was achieved by ring expansion of pyrrolidines via a regioselective attack of nucleophiles on a bicyclic azetidinium intermediate. A broad scope of azepanes, substituted at C4 and bearing a α‐trifluoromethyl, α‐difluoromethyl or α‐perfluorobutyl group, can be synthesized by this method by using a wide variety of nucleophiles. The synthesis of a variety of highly enantio‐enriched 2‐fluoroalkyl 4‐substituted azepanes was achieved using a ring expansion of pyrrolidines via an azetidinium intermediate. This reaction is regioselective and a broad scope of nucleophiles can be used which gives access to a great diversity of substituted azepanes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900613