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The Fluorine‐Iminium Ion Gauche Effect: Proof of Principle and Application to Asymmetric Organocatalysis
Author(s) -
Sparr Christof,
Schweizer W. Bernd,
Senn Hans Martin,
Gilmour Ryan
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900405
Subject(s) - iminium , organocatalysis , chemistry , stereoselectivity , amine gas treating , ion , fluorine , counterion , catalysis , organic chemistry , enantioselective synthesis
The gauche effect that is induced upon reversible formation of an iminium ion (see structure: green F, blue N) provides a powerful method for the preorganization of transient intermediates that are central to secondary amine catalyzed processes. This phenomenon has been exploited in the design of a novel organocatalyst and is showcased in the stereoselective epoxidation of α,β‐unsaturated aldehydes.