26480-64-8Relevant academic research and scientific papers
Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
Peters, Bram B. C.,Jongcharoenkamol, Jira,Krajangsri, Suppachai,Andersson, Pher G.
, p. 242 - 246 (2021/01/13)
Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.
Stereodivergent Evolution of Artificial Enzymes for the Michael Reaction
Garrabou, Xavier,Macdonald, Duncan Stuart,Wicky, Basile I. M.,Hilvert, Donald
supporting information, p. 5288 - 5291 (2018/04/06)
Enzymes are valuable biocatalysts for asymmetric synthesis due to their exacting stereocontrol. Changing the selectivity of an existing catalyst for new applications is, however, challenging. Here we show that, in contrast, the stereoselectivity of an art
Crystal structures, in-silico study and anti-microbial potential of synthetic monocarbonyl curcuminoids
Ud Din, Zia,Serrano,Ademi, Kastriot,Sousa,Deflon, Victor Marcelo,Maia, Pedro Ivo da Silva,Rodrigues-Filho, Edson
, p. 529 - 534 (2017/05/26)
In this work the screening of 20 unsymmetrical chalcone and curcuminoids analogues in regard of their antimicrobial properties was conducted. Electron donating groups in the aromatic rings in the chalcone and curcuminoid derivatives produced higher antimicrobial effect. Compounds 1, 9 and 15 exhibited good activity against Escherichia coli and Staphylococcus aureus. These compounds were further evaluated against nine micro-organisms of pathological interest. Pharmmaper was used for target fishing of compounds against important bacterial targets. Molecular Docking helped to verify the results of these compounds against the selected bacterial target D-alanyl-D-alanine carboxypeptidase (PDB ID: 1PW1). The crystal structure of ligand and docked conformers in the active site of 1PW1 were analyzed. As a result structure-activity relationships are proposed. Structures of compounds 14 and 16 were obtained through single crystals X-ray diffraction studies. Compound 14 crystallizes in monoclinic space group P21/c with unit cell dimensions a = 13.1293(3) ?, b = 17.5364(4) ?, c = 15.1433(3) ?, β = 95.6440(10), V = 3469.70(13) ?3 and Z = 8. Compound 16 crystallizes in triclinic space group Pī with unit cell dimensions a = 6.8226(4) ?, b = 7.2256(4) ?, c = 18.1235(12) ?, β = 87.322(4), V = 850.57(9) ?3 and Z = 2.
Unsymmetrical 1,5-diaryl-3-oxo-1,4-pentadienyls and their evaluation as antiparasitic agents
Ud Din, Zia,Fill, Taicia Pacheco,De Assis, Francisco Favaro,Lazarin-Bidóia, Danielle,Kaplum, Vanessa,Garcia, Francielle Pelegrin,Nakamura, Celso Vataru,De Oliveira, Kleber Thiago,Rodrigues-Filho, Edson
, p. 1121 - 1127 (2014/02/14)
In this work the synthesis and antiparasitical activity of new 1,5-diaryl-3-oxo-1,4-pentadienyl derivatives are described First, compounds 1a, 1b, 1c and 1d were prepared by acid-catalyzed aldol reaction between 2-butanone and benzaldehyde, anisaldehyde, p-N,N-dimethylaminobenzaldehyde and p-nitrobenzaldehyde Reacting each of the methyl ketones 1a, 1b, 1c and 1d with the p-substituted benzaldehydes under basic-catalyzed aldol reaction, we further prepared compounds 2a-2p All twenty compounds were evaluated for antiproliferative activity, particularly for promastigote of Leishmania amazonensis and epimastigote of Trypanosoma cruzi All compounds showed good activity while nitro compounds 2i and 2k showed inhibition activity at a few μM
Enantiodivergence in the reduction of α-methyl and α-halomethyl enones by microorganisms
De Paula, Bruno R.S.,Zampieri, Davila S.,Rodrigues, J. Augusto R.,Moran, Paulo J.S.
, p. 973 - 981 (2013/09/23)
Enones (Z)-3-methyl-(Z)-3-chloromethyl- and (Z)-3-bromomethyl-4-R-3-buten- 2-one (R = n-pentyl, phenyl, 2′- and 4′-chlorophenyl, 3′- and 4′-nitrophenyl, 4′-methoxyphenyl) were synthesized and subjected to reduction by the microorganisms Saccharomyces cerevisiae andGeotrichum candidum. Whereas the bioreduction of 3-methy-4-R-3-buten-2-ones afforded the corresponding (S)-4-R-3-methybutan-2-ones, the bioreduction of 3-chloromethyl- and 3-bromomethyl-4-R-3-buten-2-ones afforded the corresponding (R)-4-R-3-methybutan-2-ones.
Highly diastereo- and enantioselective direct aldol reaction under solvent-free conditions
Zhang, Furen,Li, Chunmei,Qi, Chenze
, p. 380 - 388 (2013/06/27)
An efficient, solvent-free protocol for the asymmetric aldol reaction between aldehydes and ketones using prolinamides 1-4 as organocatalysts is reported. Catalysts 2-4, in the presence of TFA (the ratio of catalyst and TFA = 1/1.5), proved to be excellen
CuH-catalyzed enantioselective 1,2-reductions of α,β-unsaturated ketones
Moser, Ralph,Boskovia, Zarko V.,Crowe, Christopher S.,Lipshutz, Bruce H.
supporting information; experimental part, p. 7852 - 7853 (2010/08/04)
The first study on a general technology for arriving at valued nonracemic allylic alcohols using asymmetric ligand-accelerated catalysis by copper hydride is described.
Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydrogenation
Lu, Sheng-Mei,Bolm, Carsten
supporting information; experimental part, p. 8920 - 8923 (2009/05/30)
(Chemical Equation Presented) Close to perfect enantioselectivity (up to 99% ee, see scheme) is found for the formation of α-substituted ketones by the asymmetric hydrogenation of enones with an iridium-phosphinooxazoline catalyst. In an operationally simple process, both linear and cyclic substrates react well and afford the desired products in high yields. A wide variety of substituents are tolerated, thus making the method synthetically appealing.
The Knoevenagel Reactions of Aldehydes with Carboxy Compounds. I. Reactions of p-Nitrobenzaldehyde with Active Methine Compounds
Tanaka, Mayumi,Oota, Osamu,Hiramatsu, Hideo,Fujiwara, Kazuyoshi
, p. 2473 - 2480 (2007/10/02)
The Knoenvenagel reactions of p-nitrobenzaldehyde (1) with β-keto acids, methylmalonic (2a) and α-methylacetoacetic acids (2b) were carried out in the presence of a tertiary amine such as pyridine.We have isolated the corresponding β-hydroxy intermediate
