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- W2951072009 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 benefiting from favourable stereoelectronic and electrostatic interactions (σC−H→σC−F*; Fδ−…N+). Consequently, one of the shielding groups on the fluorine-bearing carbon atom is positioned above the π-system, forming the basis of an enantioinduction strategy. Treatment of this intermediate with a “nitrene” source furnished a series of novel, optically active aziridines (e.r. up to 99.5:0.5). Further derivatisation of the product aziridines gives facile access to various amino acid derivatives, including β-fluoroamino acids. Crystallographic analyses of both the aziridines and their derivatives are disclosed." @default.
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- W2951072009 date "2014-06-26" @default.
- W2951072009 modified "2023-09-23" @default.
- W2951072009 title "ChemInform Abstract: Enantioselective Aziridination of Cyclic Enals Facilitated by the Fluorine-Iminium Ion Gauche Effect." @default.
- W2951072009 cites W2039126203 @default.
- W2951072009 doi "https://doi.org/10.1002/chin.201428086" @default.
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