69390-24-5Relevant 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.
supporting information, 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.
Hydroperoxidations of Alkenes using Cobalt Picolinate Catalysts
Peralta-Neel, Zulema,Woerpel
supporting information, p. 5002 - 5006 (2021/06/30)
Hydroperoxides were synthesized in one step from various alkenes using Co(pic)2as the catalyst with molecular oxygen and tetramethyldisiloxane (TMDSO). The hydration product could be obtained using a modified catalyst, Co(3-mepic)2, with molecular oxygen and phenylsilane. Formation of hydroperoxides occurred through a rapid Co-O bond metathesis of a peroxycobalt compound with isopropanol.
Extractive biocatalysis in the asymmetric reduction of α-alkyl, β-aryl enones by Baker's yeast
Silva, Rafaela M.,Okano, Laura T.,Rodrigues, J. Augusto R.,Clososki, Giuliano C.
, p. 939 - 944 (2017/07/11)
We prepared various chiral α-alkyl, β-aryl ketones with good to excellent enantiomeric excess through the Baker's yeast asymmetric double-bond reduction of the corresponding α,β-unsaturated substrates adsorbed onto the resin Amberlite XAD-7. This methodology was compatible with substrates bearing both electron-donating and withdrawing groups attached to the aromatic ring. Elongation of the α-alkyl substituent of the starting material strongly affected the reactivity and enantioselectivity of the reaction.
Substrate scope and synthetic applications of the enantioselective reduction of α-alkyl-β-arylenones mediated by Old Yellow Enzymes
Brenna, Elisabetta,Cosi, Sara Lucia,Ferrandi, Erica Elisa,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Sacchetti, Alessandro
supporting information, p. 2988 - 2996 (2013/07/25)
The ene-reductases mediated bioreduction of a selection of open-chain α-alkyl-β-aryl enones afforded the corresponding saturated α-chiral ketones in high yield and optical purity in several cases. The stereo-electronic requirements of the reaction have been investigated, considering the nature and location of substituents on the aromatic ring as well as the steric hindrance at the α-position and adjacent to the carbonyl functionality. The general considerations drawn allow us to guide the design of α,β-unsaturated ketones to be employed as substrates of ene-reductases in future preparative applications. An interesting case of orthogonality between enzyme-based and substrate-based stereocontrol within the highly homologous ene-reductases from Saccharomyces species (OYE1-3) has been reported and rationalized with the help of computational docking studies. Furthermore, to demonstrate the synthetic versatility of the reaction, the key chiral precursors of biologically active compounds such as (2′R)- stenusines and (S)-iopanoic acid were obtained. The very robust protocol allowed us to run the reactions on preparative scale in quantitative yields, with a simple work-up and no chromatographic purification steps. The Royal Society of Chemistry 2013.
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.
Aldol condensations of aldehydes and ketones catalyzed by rare earth(III) perfluorooctane sulfonates in fluorous solvents
Yi, Wen-Bin,Cai, Chun
, p. 1553 - 1558 (2007/10/03)
Rare earth(III) perfluorooctane sulfonates (RE(OPf)3) catalyze the efficient aldol condensation of different ketones with various aromatic aldehydes in fluorous solvents without the occurrence of any self-condensations. By simple separation of the fluorous phase containing only catalyst, reaction can be repeated several times.
Double Michael addition reactions of some new 1,5-diaryl-2-alkyl-1,4-pentadien-3-ones: Part II
Padmavathi,Ramana Reddy,Venugopal Reddy,Audisesha Reddy,Bhaskar Reddy
, p. 667 - 673 (2007/10/03)
The reactivity of unsymmetrical 1,5-diaryl-2-alkyl-l,4-pentadien-3-ones with active methylene compounds has been studied. The structures of the compounds have been established by spectral parameters.
RuCl3 catalyses aldol condensations of aldehydes and ketones
Iranpoor, Nasser,Kazemi, Foad
, p. 9475 - 9480 (2007/10/03)
Anhydrous RuCl3 catalyses the efficient cross aldol condensations of different ketones with various aromatic aldehydes in sealed tube under solvent free conditions without the occurrence of any self condensations. Regioselective self condensation reaction of some ketones and aldehydes are also described. The catalytic effect of Ru(III) is shown by performing similar reactions under thermal conditions without catalyst.
Stereospecific synthesis of methyl vinyl ketones
Chamakh,M'hirsi,Amri
, p. 1157 - 1163 (2007/10/03)
A stereospecific synthesis of enones 3 by coupling reaction of α-acetoxy alkyl methyl vinyl ketones 2 and Gilman or Grignard reagents in the presence of a catalytic amount of copper(I) salt at low temperature, is described.
