|
|||||
|
|
The Fluorine‐Iminium Ion Gauche Effect: Proof of Principle and Application to Asymmetric Organocatalysis |
|
| Authors: | Christof Sparr W Bernd Schweizer Dr Hans Martin Senn Dr Ryan Gilmour Prof Dr |
| Institution: | 1. Swiss Federal Institute of Technology (ETH) Zurich, Laboratory for Organic Chemistry, Department of Chemistry and Applied Biosciences, Wolfgang‐Pauli‐Strasse 10, 8093 Zurich (Switzerland), http://www.gilmour.ethz.ch;2. WestCHEM and Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, Scotland (UK) |
| Abstract: | 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.  |
| Keywords: | chirality conformational analysis epoxidation organocatalysis organofluorine chemistry |