1524-15-8Relevant academic research and scientific papers
Rhodium-Catalyzed Enantioselective Defluorinative α-Arylation of Secondary Amides
Jang, Young Jin,Rose, Daniel,Mirabi, Bijan,Lautens, Mark
, p. 16147 - 16151 (2018)
We exploited the reactivity of an electronically biased Michael acceptor to perform a defluorinative α-arylation reaction using a chiral diene(L*)-rhodium catalyst. Through this methodology, we are able to obtain various secondary amides, containing a tertiary α-stereocenter and a β,γ-unsaturated gem-difluoro olefin, with excellent enantioselectivities. This methodology addresses the limitations of the previously described α-arylation methods to construct stereo-labile tertiary α-stereocenters. Further investigation of the reaction via in situ 19F NMR monitoring suggests that the formation of the product leads to the inhibition of the active rhodium catalyst.
Pyrrolidine as an efficient organocatalyst for direct aldol reaction of trifluoroacetaldehyde ethyl hemiacetal with ketones
Zhang, Fanglin,Peng, Yiyuan,Liao, Saihu,Gong, Yuefa
, p. 4636 - 4641 (2007)
Pyrrolidine-catalyzed aldol reaction of trifluoroacetaldehyde ethyl hemiacetal (1) with ketones or aldehydes was described. In the presence of 20 mol % of pyrrolidine, the reaction proceeded smoothly at room temperature to afford the aldol products in goo
Efficient generation of trifluoroacetaldehyde and successive reaction with imines affording β-hydroxy-β-trifluoromethyl ketones
Funabiki, Kazumasa,Matsunaga, Kei,Matsui, Masaki,Shibata, Katsuyoshi
, p. 1477 - 1479 (1999)
The reaction of trifluoroacetaldehyde ethyl hemiacetal or hydrate with an equimolar amount of imine in hexane at reflux temperature for 1 h gave the corresponding β-hydroxy-β-trifluoromethyl ketones in good to excellent yields.
The use of trifluoroacetaldehyde ethyl hemiacetal or hydrate in a simple and practical regioselective synthesis of β-hydroxy-β-trifluoromethyl ketones from enamines and imines
Funabiki, Kazumasa,Matsunaga, Kei,Nojiri, Miwa,Hashimoto, Wataru,Yamamoto, Hitoshi,Shibata, Katsuyoshi,Matsui, Masaki
, p. 2853 - 2860 (2003)
The reaction of trifluoroacetaldehyde ethyl hemiacetal or hydrate with an equimolar amount of enamines, derived from various methyl ketones, smoothly proceeded to give the corresponding β-hydroxy-β-trifluoromethyl ketones in high yields. An equimolar amou
Enamine-assisted facile generation of trifluoroacetaldehyde from trifluoroacetaldehyde ethyl hemiacetal and its carbon-carbon bond forming reaction leading to β-hydroxy-β-trifluoromethyl ketones
Funabiki, Kazumasa,Nojiri, Miwa,Matsui, Masaki,Shibata, Katsuyoshi
, p. 2051 - 2052 (1998)
Trifluoroacetaldehyde ethyl hemiacetal 1 readily reacts with various enamines 2 in hexane at room temperature for l h to give the corresponding β-hydroxy-β-trifluoromethyl ketones in good yields.
Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones
Ramasamy, Manickavasakam,Lin, Hui-Chang,Kuo, Sheng-Chu,Hsieh, Min-Tsang
, p. 356 - 360 (2019/02/12)
A practical Lewis acid-catalyzed Meyer-Schuster rearrangement of fluoroalkylated propargylic alcohols, leading to a series of β-fluoroalkyl-α,β-enones, is developed. The methodology reported herein features moderate to high yields and high stereoselectivi
Rh(III)-Catalyzed [3 + 2] Annulation via C-H Activation: Direct Access to Trifluoromethyl-Substituted Indenamines and Aminoindanes
Chaudhary, Bharatkumar,Auti, Prashant,Shinde, Suchita Dattatray,Yakkala, Prasanna Anjaneyulu,Giri, Deepesh,Sharma, Satyasheel
supporting information, p. 2763 - 2767 (2019/04/30)
The rhodium(III)-catalyzed direct C-H addition and annulation of benzimidates and aldimines with β-(trifluoromethyl)-α,β-unsaturated ketones is described. This protocol provides the facile and efficient formation of various trifluoromethyl-containing inde
Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao
supporting information, p. 5040 - 5045 (2019/07/03)
(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts
Vitale, Paola,Perna, Filippo Maria,Agrimi, Gennaro,Scilimati, Antonio,Salomone, Antonio,Cardellicchio, Cosimo,Capriati, Vito
supporting information, p. 11438 - 11445 (2016/12/16)
Regio- and stereo-selective reduction of substituted 1,3-aryldiketones, investigated in the presence of different whole cell microorganisms, was found to afford β-hydroxyketones or 1,3-diols in very good yields (up to 95%) and enantiomeric excesses (up to 96%). The enantiomerically enriched aldols, obtained with the opposite stereo-preference by baker's yeast and Lactobacillus reuteri DSM 20016 bioreduction, could then be diastereoselectively transformed into optically active syn- or anti-1,3-diols by a careful choice of the chemical reducing agent (diastereomeric ratio up to 98 : 2). The latter, in turn, were stereospecifically cyclized into the corresponding oxetanes in 43-98% yields and in up to 94% ee, thereby giving a diverse selection of stereo-defined 2,4-disubstituted aryloxetanes.
Rhodium(III)-catalyzed sp2 C-H bond addition to CF3-substituted unsaturated ketones
Jiang, Quanbin,Guo, Tenglong,Wu, Kaikai,Yu, Zhengkun
supporting information, p. 2913 - 2915 (2016/02/19)
Rhodium(iii)-catalyzed conjugate addition of aromatic and olefinic C-H bonds to CF3-substituted unsaturated ketones was efficiently achieved. Both arene and olefin substrates bearing a chelate assisted-directing group were coupled with a variet
