Premium
CarbonCarbon Bond Cleavage with Inversion of Configuration: Conversion of ( R )‐(+)‐1‐Methoxytetrafluoropropionic Acid to ( S )‐(−)‐1,2,2,2‐Tetrafluoroethyl Methyl Ether
Author(s) -
Ramig Keith,
Brockunier Linda,
Rafalko Patrice W.,
Rozov Leonid A.
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199502221
Subject(s) - chemistry , enantiomer , decarboxylation , ether , cleavage (geology) , inversion (geology) , walden inversion , stereochemistry , bond cleavage , potassium , medicinal chemistry , organic chemistry , materials science , catalysis , geology , paleontology , structural basin , fracture (geology) , composite material
Nearly complete inversion of configuration is seen during decarboxylation of the potassium salt 1 of an α‐chiral carboxylic acid to give ether 2 . Since 2 is an intermediate in the synthesis of inhalational anesthetics, and its enantiomers may have different pharmacological profiles, the determination of the stereochemical outcome of this CC bond cleavage is of particular interest.