128404-37-5Relevant academic research and scientific papers
Thermal 1,3-proton shift reaction and its application for operationally convenient and improved synthesis of α-(trifluoromethyl)benzylamine
Yasumoto, Manabu,Ueki, Hisanori,Soloshonok, Vadim A.
, p. 736 - 739 (2007)
This paper describes a synthesis of α-(trifluoromethyl)benzylamine via a novel base-free biomimetic reductive amination of α,α,α-trifluoroacetophenone with benzylamine. When the corresponding imine, derived from α,α,α-trifluoroacetophenone and benzylamine
METHOD FOR PRODUCING OPTICALLY ACTIVE TRIFLUOROMETHYL GROUP-CONTAINING AMINO ACID DERIVATIVE
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Paragraph 0123; 0124; 0125; 0126; 0127, (2019/02/28)
PROBLEM TO BE SOLVED: To provide methods for producing optically active trifluoromethyl group-containing sulfinamide derivatives and optically active amino acids/hydrochlorides, using trifluoromethane as a generator of trifluoromethyl anions. SOLUTION: Th
Stereodivergent trifluoromethylation of: N -sulfinylimines by fluoroform with either organic-superbase or organometallic-base
Punna, Nagender,Saito, Takuya,Kosobokov, Mikhail,Tokunaga, Etsuko,Sumii, Yuji,Shibata, Norio
supporting information, p. 4294 - 4297 (2018/05/07)
Here we have successfully demonstrated the first stereodivergent direct nucleophilic trifluoromethylation of N-sulfinylimines using the potent greenhouse gas "HFC-23, fluoroform" with an organic-superbase or an organometallic-base in high yields and selectivity.
Palladium(II)-catalyzed enantioselective synthesis of α- (trifluoromethyl)arylmethylamines
Johnson, Thomas,Lautens, Mark
supporting information, p. 4043 - 4045 (2013/09/12)
Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium(II) catalysis to generate a variety of α-(trifluoromethyl)arylmethylamines with good to high enantioselectivity (up to 97% ee). The pyridine-oxazolidine (PyOX) class of ligands was found to be particularly suitable for this transformation, which proceeds without exclusion of ambient air and moisture.
Diastereoselective addition of organomagnesium and organolithium reagents to chiral trifluoromethyl N-tert-butanesulfinyl hemiaminals
Grellepois, Fabienne,Ben Jamaa, Abdelkhalek,Gassama, Abdoulaye
supporting information, p. 6694 - 6701 (2013/11/06)
The asymmetric synthesis of trifluoromethylated tertiary and secondary carbinamines (α,α-dibranched and α-branched amines) was achieved by reaction of alkyl, aryl and allyl organomagnesium or organolithium reagents to trifluoromethyl N-tert-butanesulfinyl
Thermocontrolled benzylimine-benzaldimine rearrangement over Nafion-H catalysts for efficient entry into α-trifluoromethylbenzylamines
Prakash, G.K. Surya,Glinton, Kevin E.,Panja, Chiradeep,Gurung, Laxman,Battamack, Patrice T.,T?r?k, Béla,Mathew, Thomas,Olah, George A.
experimental part, p. 607 - 611 (2012/02/13)
Nafion-H and Nafion SAC-13 are efficient solid Br?nsted acid catalysts for the preparation of trifluoromethyl ketimines from benzylamines and trifluoromethylated ketones in high yields. A finely tuned benzylimine- benzaldimine rearrangement by facile 1,3-hydrogen shift has been achieved for the formation of fluorinated benzaldimines in high yields by careful optimization of reaction conditions including attempts under microwave conditions and a flow system. These α-trifluoromethylated benzaldimines are efficient precursors for pharmaceutically important α- trifluoromethylated benzylamines, accessed through their direct acid hydrolysis.
One-pot asymmetric synthesis of α-trifluoromethylated amines from α-trifluoromethyl ketones
Xu, Jian,Liu, Zhen-Jiang,Yang, Xian-Jin,Wang, Li-Min,Chen, Guan-Long,Liu, Jin-Tao
supporting information; experimental part, p. 8933 - 8937 (2011/01/04)
Diastereoselective reduction of (Rs)-N-tert-butanesulfinyl α-trifluoromethyl ketimines formed in situ from the corresponding α-trifluoromethyl ketones and N-tert-butanesulfinamide has been achieved, and either diastereomer of N-tert-butanesulfinyl α-trifl
Enantiodivergent approach to trifluoromethylated amines: A concise route to both enantiomeric analogues of calcimimetic NPS R-568
Fernandez, Inmaculada,Valdivia, Victoria,Alcudia, Ana,Chelouan, Ahmed,Khiar, Noureddine
experimental part, p. 1502 - 1509 (2010/06/15)
Reported herein is a straightforward and enantiodivergent synthesis of both enantiomers of trifluoromethylated analogues of calcimimetic NPS R-569 in a highly estereoselective manner. The synthesis features a diastereoselective synthesis of the N-(isopropylsulfinyl)imine unit by the "DAG methodology" and a diastereoselective addition of Ruppert Prakash's reagent to the imine as the key steps. No protecting groups were necessary, permitting an atom economic synthesis in only six steps. Further addition reactions of the CF3 anion to different N-(isopropylsulfinyl)imines were performed to demonstrate the suitability of the sulfinyl substituent to balance perfectly reactivity and diastereoselectivity.
Rhodium-catalyzed diastereoselective 1,2-addition of arylboronic acids to chiral trifluoroethyl imine
Truong, Vouy Linh,Pfeiffer, Jennifer Y.
scheme or table, p. 1633 - 1635 (2009/06/18)
Rhodium-catalyzed 1,2-addition of arylboronic acids 4a-j to chiral trifluoroethyl imine 3 afforded diastereomerically enriched sulfinamides 5a-j. The chiral auxiliary of the sulfinamide products was readily removed under acidic methanolysis to provide the corresponding trifluoroethylamine analogs 6a-j.
