The fluorine-iminium ion gauche effect: proof of principle and application to asymmetric organocatalysis.
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.
Sparr
Christof
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
W Bernd
WB
Senn
Hans Martin
HM
Gilmour
Ryan
R