The Fluorine‐Iminium Ion  Gauche  Effect: Proof of Principle and Application to Asymmetric Organocatalysis | Zendy

Sparr Christof | Zendy; Schweizer W. Bernd | Zendy; Senn Hans Martin | Zendy; Gilmour Ryan | Zendy

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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.

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