Journal article
The fluorine-iminium ion gauche effect: proof of principle and application to asymmetric organocatalysis.
- Sparr C Swiss Federal Institute of Technology (ETH) Zurich, Laboratory for Organic Chemistry, Department of Chemistry and Applied Biosciences, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland.
- Schweizer WB
- Senn HM
- Gilmour R
- 2009-03-27
Published in:
- Angewandte Chemie (International ed. in English). - 2009
English
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 alpha,beta-unsaturated aldehydes.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1002/anie.200900405
- PMID 19322862
- Persistent URL
- https://folia.unifr.ch/global/documents/164275
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