1287211-10-2Relevant academic research and scientific papers
Modulating NHC catalysis with fluorine
Rey, Yannick P.,Gilmour, Ryan
, p. 2812 - 2820 (2013)
Fluorination often confers a range of advantages in modulating the conformation and reactivity of small molecule organocatalysts. By strategically introducing fluorine substituents, as part of a β-fluoroamine motif, in a triazolium pre-catalyst, it was possible to modulate the behaviour of the corresponding N-heterocyclic carbene (NHC) with minimal steric alterations to the catalyst core. In this study, the effect of hydrogen to fluorine substitution was evaluated as part of a molecular editing study. X-ray crystallographic analyses of a number of derivatives are presented and the conformations are discussed. Upon deprotonation, the fluorinated triazolium salts generate catalytically active N-heterocyclic carbenes, which can then participate in the enantioselective Steglich rearrangement of oxazolyl carbonates to C-carboxyazlactones (e.r. up to 87.0:13.0).
Deoxofluorination of Aliphatic Carboxylic Acids: A Route to Trifluoromethyl-Substituted Derivatives
Bugera, Maksym,Trofymchuk, Serhii,Tarasenko, Karen,Zaporozhets, Olga,Pustovit, Yurii,Mykhailiuk, Pavel K.
, p. 16105 - 16115 (2019/12/24)
A practical method for the synthesis of functionalized aliphatic trifluoromethyl-substituted derivatives from aliphatic acids is developed. The transformation proceeds with sulfur tetrafluoride in the presence of water as a key additive. Compared to previous methods, the reaction gives products with full retention of stereo- and absolute configuration of chiral centers.
PRODUCTION METHOD OF OPTICALLY ACTIVE FLUORINE-CONTAINING AMINO ACID
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Paragraph 0065-0067, (2018/10/26)
PROBLEM TO BE SOLVED: To provide a production method of optically active fluorine-containing amino acids useful as a synthetic intermediate of pharmaceutical and agricultural chemicals. SOLUTION: Optically active fluorine-containing amino acids expressed by general formula (4) or general formula (5) are obtained by a radical addition reaction of a halocarboxylic acid ester to an optically active trifluoromethyl tert-butyl sulfine imide. In formula (4), R1 represents a methyl group, an ethyl group or a linear, branched or cyclic alkyl group having 3 to 4 carbon atoms; X represents a halogen atom; and n represents an integer of 1 to 5. In formula (5), R1 and n are the same as defined above. COPYRIGHT: (C)2015,JPOandINPIT
(5S)-5-(trifluoromethyl)pyrrolidin-2-one as a promising building block for fluoroorganic chemistry
Bezdudny, Andrii V.,Alekseenko, Anatoliy N.,Mykhailiuk, Pavel K.,Manoilenko, Olga V.,Shishkin, Oleg V.,Pustovit, Yurii M.
experimental part, p. 1782 - 1785 (2011/05/03)
Pyroglutamic acid smoothly reacts with sulfur tetrafluoride at room temperature to afford enantiomerically pure (5S)-5-(trifluoromethyl)pyrrolidin- 2-one (92 % yield, >99 % ee). Representative one-step transformations of 1 provided both γ-(S)-trifluoromethyl GABA and (2S)-2-(trifluoromethyl) pyrrolidine on a multigram scale. Pyroglutamic acid smoothly reacts with sulfur tetrafluoride at room temperature to afford enantiomerically pure (5S)-5-(trifluoromethyl)pyrrolidin-2-one (1; 92 %yield, >99 % ee). Representative one-step transformations of 1 provided γ-(S)- trifluoromethyl GABA and (2S)-2-(trifluoromethyl)pyrrolidine on a multigram scale. Copyright
