61780-85-6Relevant 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.
Pd-Catalyzed β-C-H Arylation of Aldehydes and Ketones Based on a Transient Directing Group
Wu, Liang-Fei,Yao, Jian-Wei,Zhang, Xin,Liu, Si-Yuan,Zhuang, Ze-Nian,Wei, Kun
supporting information, p. 6237 - 6241 (2021/08/23)
The direct Pd-catalyzed β-C-H arylation of aldehydes and ketones was developed by using 2-amino-N,N′-diisopropylsuccinamide as a novel transient directing group (TDG). The TDG showed good versatility in functionalizing unactivated β-C-H bonds of aldehydes and ketones. It was effective not only for aliphatic aldehydes and ketones but also for aromatic aldehydes and ketones. Besides, it was applicable to o-methylbenzaldehydes.
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
, 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.
Development of catalysts for the stereoselective hydrogenation of α,β-unsaturated ketones
Maurer, Frauke,Huch, Volker,Ullrich, Angelika,Kazmaier, Uli
experimental part, p. 5139 - 5143 (2012/07/03)
Iridium phosphinitoxazoline complexes were found to be new efficient catalysts for the asymmetric hydrogenation of arylated α,β- unsaturated ketones. Linear as well as cyclic substrates are hydrogenated with similar success, giving selectivities of up to 99.7% ee.
Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating hyperplasia and other diseases
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Page 30, 128, (2010/02/05)
Certain 2H-pyran-2-ones are useful for treating benign prostatic hypertrophy or hyperplasia, prostatic cancer, alopecia, hirsutism, acne vulgaris and seborrhea.
Highly Regioselective Monoalkylation of Ketones via Manganese Enolates. Prepared from Lithium Enolates
Cahiez, Gerard,Chau, Khi,Clery, Patrick
, p. 3069 - 3072 (2007/10/02)
Li-enolates are readily converted to Mn-enolates by treatment with manganese halides.In THF, the reaction is easily and economically performed with manganese chloride at room temperature.Mn-enolates can then be regioselectively monoalkylated in good yields.The formation of di and polyalkylated products is never observed (1percent).
Functional Group Hybrids. Reactivity of α'-Nucleofuge α,β-Unsaturated Ketones. 1. Reactions with Organocopper Reagents
Barbee, Thomas R.,Albizati, Kim F.
, p. 6764 - 6773 (2007/10/02)
A series of α-nucleofuge α',β'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared.Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the α-nucl
