Enantioselective Aziridination of Cyclic Enals Facilitated by the Fluorine??Iminium Ion Gauche Effect

…, EM Tanzer, C Daniliuc, R Gilmour

Index: Molnar, Istvan Gabor; Tanzer, Eva-Maria; Daniliuc, Constantin; Gilmour, Ryan Chemistry - A European Journal, 2014 , vol. 20, # 3 p. 794 - 800

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Citation Number: 19

Abstract

Abstract The enantioselective, organocatalytic aziridination of small, medium and macro- cyclic enals is reported using (S)-2-(fluorodiphenyl methyl)-pyrrolidine. Central to the reaction design is the reversible formation of a β-fluoroiminium ion intermediate, which is pre- organised on account of the fluorine-iminium ion gauche effect. This conformational effect positions the fluorine substituent synclinal-endo to the electropositive nitrogen centre thus ...