Open AccessJoy and Flustration with Organofluorine Compounds – A Fluorous Autobiography
Author(s) -
Dieter Seebàch
Publication year - 2014
Publication title -
chimia international journal for chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2014.348
Subject(s) - enantiopure drug , chemistry , fluorine , amide , peptide bond , dendrimer , amino acid , organic chemistry , reactivity (psychology) , reagent , folding (dsp implementation) , combinatorial chemistry , stereochemistry , enantioselective synthesis , catalysis , medicine , biochemistry , alternative medicine , pathology , engineering , electrical engineering
An overview is given about our work on fluoro-organic compounds, published or described in PhD theses between 1977 and 2013. After a discussion of structural F-effects and F-tagging applications the material is ordered by the various areas of our research, in which we have used and/or prepared F-derivatives: Li- and Ti-organic compounds and reagents, polylithiated hydroxy-esters and nitroalkanes, the enantiopure trifluoro-lactic, -Roche, and -3-hydroxy-butanoic acids as toolbox for the preparation of numerous F3C-substituted compounds, including natural products and dendrimers, and fluoro-?-, -?-, and -?-amino acids, as well as peptides with back-bond-bound fluorine. The strong influence on ?-peptide folding by fluoro-substituents in the ?-position of ?-amino-acid residues is discussed in terms of the ?-fluoro-amide conformational effect. Finally, some cases of totally unexpected effects on reactivity and structure exerted by fluoro-substitution are presented and taken as examples for our use of the terms flustrate and flustration in connection with organo-fluorine chemistry.
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