134418-70-5Relevant academic research and scientific papers
A convenient preparation of (±)-α-methoxy-α-trifluoromethylphenylacetic acid (Mosher's acid)
Chong,Loewith
, p. 2145 - 2150 (1993)
Mosher's acid can be prepared from PhC(O)CF3 via a vinylation, methylation, ozonolysis/oxidation sequence in >80% overall yield.
Asymmetric Synthesis of α,α-Disubstituted Allylic Amines through Palladium-Catalyzed Allylic Substitution
Guo, Wusheng,Cai, Aijie,Xie, Jianing,Kleij, Arjan W.
, p. 11797 - 11801 (2017)
The first asymmetric synthesis of important α,α-disubstituted N-alkyl allyl amine scaffolds through allylic substitution is reported. This approach is based on palladium catalysis and features ample scope with respect to both the allylic precursor and amine reagent, and high asymmetric induction with enantiomeric ratios (e.r.) up to 98.5:1.5. The use of less-reactive anilines is also feasible, providing enantioenriched α,α-disubstituted N-aryl allylic amines.
Domino Synthesis of α,β-Unsaturated γ-Lactams by Stereoselective Amination of α-Tertiary Allylic Alcohols
Xie, Jianing,Xue, Sijing,Escudero-Adán, Eduardo C.,Kleij, Arjan W.
supporting information, p. 16727 - 16731 (2018/11/23)
Tertiary allylic alcohols equipped with a carboxyl group can be smoothly aminated under ambient conditions by a conceptually new and stereoselective protocol under palladium catalysis. The in situ formed Z-configured γ-amino acid cyclizes to afford an α,β-unsaturated γ-lactam, releasing water as the only byproduct. This practical catalytic transformation highlights the use of a carboxyl group acting as an activating and stereodirecting functional group to provide a wide series of pharma-relevant building blocks. Various control reactions support the crucial role of the carboxyl group in the substrate to mediate these transformations.
A convergent, unified approach to functionalized fluoro- and trifluoromethyl alkenes
Debien, Laurent,Quiclet-Sire, Beatrice,Zard, Samir S.
supporting information, p. 5118 - 5121,4 (2012/12/12)
A modular, convergent, and operationally simple route to trifluoromethyl alkenes and vinyl fluorides involving a unique carbon-oxygen bond homolysis is reported. Highly functionalized trifluoromethyl alkenes and vinyl fluorides were obtained in good yield
An enzymatic toolbox for the kinetic resolution of 2-(Pyridin-x-yl)but-3- yn-2-ols and tertiary cyanohydrins
Nguyen, Giang-Son,Kourist, Robert,Paravidino, Monica,Hummel, Anke,Rehdorf, Jessica,Orru, Romano V. A.,Hanefeld, Ulf,Bornscheuer, Uwe T.
experimental part, p. 2753 - 2758 (2010/07/06)
The kinetic resolution of a series of acetates of tertiary alcohols bearing a nitrogen substituent has been studied by using several recombinant carboxyl esterases and variants thereof expressed in E. coli. Most of the enzymes were active in the conversion of these tertiary alcohols and excellent enantioselectivities were achieved in the synthesis of three 2-(pyridin-x-yl)but-3-yn-2-ols with the nitrogen atom in the pyridine ring in the 2′-, 3′-, and 4′-positions. The resolution of tertiary cyanohydrins proved to be more difficult as the enantioselectivity of the enzymes was generally lower. Nevertheless, (S)-1-cyano-2,2,2-trifluoro-1- phenylethyl acetate was obtained with 99% ee. The results show that the limited substrate range of the individual enzymes in the synthesis of a series of tertiary alcohols can be efficiently overcome by using a combination of different enzymes.
Highly enantioselective synthesis of arylaliphatic tertiary alcohols using mutants of an esterase from Bacillus subtilis
Kourist, Robert,Bartsch, Sebastian,Bornscheuer, Uwe T.
, p. 1393 - 1398 (2008/03/28)
The kinetic resolution of a series of acetates of arylaliphatic tertiary alcohols was studied using recombinant esterase variants from Bacillus subtilis (BS2) expressed in E. coli. Highest enantioselectivities (E > 100) were achieved in the synthesis of 1
Synthese d'Amines Primaires Allyliques γ-trifluoromethylees
Felix, Caroline,Laurent, Andre,Lebideau, Franck,Mison, Pierre
, p. 2627 - 2648 (2007/10/02)
Des amines primaires allyliques substituees par un groupement trifluoromethyle ont ete preparees par une voie de synthese faisant intervenir intermediairement des azotures allyliques.Deux autres approches d'obtention de ces amines ont ete essayees: reacti
Synthesis of Perfluoroalkylated Indenes
Gassman, Paul G.,Ray, Julia A.,Wenthold, Paul G.,Mickelson, John W.
, p. 5143 - 5146 (2007/10/02)
A series of perfluoroalkylated indenes has been synthesized using four different synthetic pathways. 1-(Pentafluoroethyl)indene and 2-(pentafluoroethyl)indene were prepared by the addition of (pentafluoroethyl)lithium to the appropriate ketones and subseq
