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(5 S )‐5‐(Trifluoromethyl)pyrrolidin‐2‐one as a Promising Building Block for Fluoroorganic Chemistry
Author(s) -
Bezdudny Andrii V.,
Alekseenko Anatoliy N.,
Mykhailiuk Pavel K.,
Manoilenko Olga V.,
Shishkin Oleg V.,
Pustovit Yurii M.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001362
Subject(s) - trifluoromethyl , chemistry , yield (engineering) , pyrrolidine , organic chemistry , block (permutation group theory) , pyroglutamic acid , medicinal chemistry , amino acid , metallurgy , biochemistry , alkyl , materials science , geometry , mathematics
Pyroglutamic acid smoothly reacts with sulfur tetrafluoride at room temperature to afford enantiomerically pure (5 S )‐5‐(trifluoromethyl)pyrrolidin‐2‐one (92 % yield, >99 % ee ). Representative one‐step transformations of 1 provided both γ‐( S )‐trifluoromethyl GABA and (2 S )‐2‐(trifluoromethyl)pyrrolidine on a multigram scale.