The fluorine-iminium ion gauche effect: proof of principle and application to asymmetric organocatalysis

Sparr, C., Schweizer, W.B., Senn, H.M. and Gilmour, R. (2009) The fluorine-iminium ion gauche effect: proof of principle and application to asymmetric organocatalysis. Angewandte Chemie (International Edition), 48(17), pp. 3065-3068. (doi: 10.1002/anie.200900405)

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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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Senn, Dr Hans
Authors: Sparr, C., Schweizer, W.B., Senn, H.M., and Gilmour, R.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Angewandte Chemie (International Edition)
Journal Abbr.:Angew Chem Int Ed Engl
Publisher:Wiley - V C H Verlag GmbH & Co. KGaA
ISSN:1433-7851
ISSN (Online):1521-3773
Published Online:25 March 2009

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