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Remarkable Amplification of the Self‐Disproportionation of Enantiomers on Achiral‐Phase Chromatography Columns
Author(s) -
Soloshonok Vadim A.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200503373
Subject(s) - stereocenter , disproportionation , enantiomer , fluorine , reagent , chemistry , silica gel , trifluoromethyl , phase (matter) , carbon fibers , organic chemistry , stereochemistry , materials science , enantioselective synthesis , alkyl , catalysis , composite number , composite material
A phase they're going through : The enantiomers of chiral compounds containing a trifluoromethyl group directly bonded to a stereogenic carbon center are prone to self‐disproportionation on columns of achiral silica gel (see picture). Thus, all fluorine‐containing chiral reagents and drugs, as well as literature data on the stereochemical outcome of asymmetric transformations involving fluorine‐containing compounds, should be reevaluated.