(5 S )‐5‐(Trifluoromethyl)pyrrolidin‐2‐one as a Promising Building Block for Fluoroorganic Chemistry | Zendy

Bezdudny Andrii V. | Zendy; Alekseenko Anatoliy N. | Zendy; Mykhailiuk Pavel K. | Zendy; Manoilenko Olga V. | Zendy; Shishkin Oleg V. | Zendy; Pustovit Yurii M. | Zendy

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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.

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