title: The fluorine-iminium ion gauche effect: proof of principle and application to asymmetric organocatalysis.
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 alpha,beta-unsaturated aldehydes.
authors.affiliation: Swiss Federal Institute of Technology (ETH) Zurich, Laboratory for Organic Chemistry, Department of Chemistry and Applied Biosciences, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland.
authors.forename: Christof
authors.initials: C
authors.lastname: Sparr
authors.forename: W Bernd
authors.initials: WB
authors.lastname: Schweizer
authors.forename: Hans Martin
authors.initials: HM
authors.lastname: Senn
authors.forename: Ryan
authors.initials: R
authors.lastname: Gilmour