15175-34-5Relevant academic research and scientific papers
β′-Hydroxy-α,β-unsaturated ketones: A new pharmacophore for the design of anticancer drugs
Padrón, José M.,Miranda, Pedro O.,Padrón, Juan I.,Martín, Víctor S.
, p. 2266 - 2269 (2006)
A series of β′-hydroxy-α,β-unsaturated ketones were prepared by means of an iron(III) catalyzed domino process. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, SW1573, and WiDr. The results showed that β′
Acyl/aroyl Meldrum's acid as an enol surrogate for the direct organocatalytic synthesis of α,β-unsaturated ketones
Khopade, Tushar M.,Warghude, Prakash K.,Mete, Trimbak B.,Bhat, Ramakrishna G.
, p. 197 - 200 (2018/12/13)
The operationally simple, robust and straightforward organocatalytic protocol is developed for the synthesis of E-selective α,β-unsaturated ketones. The method utilizes simple and easily accessible starting materials such as Meldrum's acid, carboxylic acid, aldehyde and simple bifunctional amine catalyst. The tandem organocatalytic process utilizes acyl/aroyl Meldrum's acid as an enol surrogate for the effective Doebner-Knoevenagel type condensation reactions. A wide variety of aldehydes, carboxylic acids and base sensitive functional groups are well tolerated under the mild reaction conditions.
Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
supporting information, p. 2003 - 2006 (2018/04/16)
A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p
A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides
Bi, Hong-Yan,Liu, Feng-Ping,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
supporting information, p. 1510 - 1516 (2018/03/05)
A tunable strategy to prepare α,β-unsaturated esters and α,β-unsaturated-γ-keto esters in good to excellent yields was developed through copper-catalyzed oxidative coupling of phosphorus ylides with alkenyl boronic acids under mild conditions. The reaction without water afforded α,β-unsaturated esters, ketones, and amides while α,β-unsaturated-γ-keto esters, 1,4-α,β-unsaturated diketones and α,β-unsaturated-γ-keto amides were obtained when using 5.0 equiv. of water. H2O18 labeling experiments showed that water played an important role in the formation of α,β-unsaturated-γ-keto esters. A plausible formation mechanism for α,β-unsaturated esters and α,β-unsaturated-γ-keto esters was proposed based on mechanistic studies. Phosphonium salts could also be used directly as coupling partners instead of phosphorus ylides. The reaction exhibited a broad substrate scope, good functional group tolerance, good regioselectivity, and diverse coupling products. (Figure presented.).
Alkyne Difunctionalization by Dual Gold/Photoredox Catalysis
Tlahuext-Aca, Adrian,Hopkinson, Matthew N.,Aleyda Garza-Sanchez,Glorius, Frank
supporting information, p. 5909 - 5913 (2016/04/26)
Highly selective tandem nucleophilic addition/cross-coupling reactions of alkynes have been developed using visible-light-promoted dual gold/photoredox catalysis. The simultaneous oxidation of AuI and coordination of the coupling partner by photo-generated aryl radicals, and the use of catalytically inactive gold precatalysts allows for high levels of selectivity for the cross-coupled products without competing hydrofunctionalization or homocoupling. As demonstrated in representative arylative Meyer-Schuster and hydration reactions, this work expands the scope of dual gold/photoredox catalysis to the largest class of substrates for gold catalysts and benefits from the mild and environmentally attractive nature of visible-light activation. United we stand! Tandem nucleophilic addition/cross-coupling reactions have been developed with challenging alkynes using a visible-light-promoted dual gold/photoredox catalytic system (see scheme). High levels of selectivity for the cross-coupled products were obtained without competition from the homocoupling or conventional hydrofunctionalization.
A convenient synthesis of 4-alkyl-3-benzoylpyrroles from α,β-unsaturated ketones and tosylmethyl isocyanide
Kumar, Kapil,More, Shital S.,Goyal, Sandeep,Gangar, Mukesh,Khatik, Gopal L.,Rawal, Ravindra K.,Nair, Vipin A.
supporting information, p. 2315 - 2319 (2016/05/10)
A convenient synthesis of 4-alkyl-3-benzoyl pyrrole was achieved from α,β-unsaturated ketones and tosylmethyl isocyanide in the presence of mild base LiOH·H2O. This method is very economical and was successfully utilized for the synthesis of various 4-alkyl-3-benzoylpyrrole derivatives with good to excellent yields.
Barluenga's reagent with HBF4 as an efficient catalyst for alkyne-carbonyl metathesis of unactivated alkynes
Murai, Kosuke,Tateishi, Keiichiro,Saito, Akio
supporting information, p. 10352 - 10356 (2016/11/18)
Barluenga's reagent (IPy2BF4, Py = pyridine) treated with HBF4 efficiently catalyzes the inter- and intramolecular alkyne-carbonyl metathesis of unactivated alkynes with aldehydes or ketones, most of which proceed at room temperature. This work represents the first catalytic application of the Barluenga's reagent.
Rasta Resin-PPh3-NBniPr2 and its use in one-pot wittig reaction cascades
Teng, Yan,Lu, Jinni,Toy, Patrick H.
experimental part, p. 351 - 359 (2012/04/18)
A new triarylphosphine-tertiary amine bifunctional polymeric reagent has been prepared and used effectively in a variety of one-pot Wittig reactions. The design of this reagent resolved a deficiency of a previously reported related material, and allowed it to perform more efficiently in such reactions. Furthermore, it was readily recyclable, and was also successfully applied in cascade processes involving one-pot Wittig reactions followed by either a conjugate reduction or a reductive aldol reaction. In these reaction cascades, the phosphine oxide groups generated in the Wittig reaction served as the catalyst for the subsequent reaction. All in one pot! A recyclable, second-generation heterogeneous bifunctional polymer bearing phosphine and amine groups has been synthesized and showed enhanced utility in one-pot Wittig reactions compared to a previously reported related material. This polymer was also used in Wittig reaction cascade processes in which the oxidized polymer formed in the one-pot Wittig reaction served as the catalyst in a subsequent conjugate reduction or reductive aldol reaction (see scheme).
Structural study-guided development of versatile phase-transfer catalysts for asymmetric conjugate additions of cyanide
Provencher, Brian A.,Bartelson, Keith J.,Liu, Yan,Foxman, Bruce M.,Deng, Li
, p. 10565 - 10569 (2011/12/05)
Unprecedented phase-transfer catalysts for the first example of an organocatalytic asymmetric conjugate addition of cyanide with acetone cyanohydrin are reported (see scheme). Utilizing an accessible cupreidinium salt and a cyanation reagent suitable for industrial scale, this reaction holds significant promise for practical asymmetric synthesis. The catalysts were developed as a result of key structural insights gained by X-ray analysis. Copyright
Iron(III)-catalyzed cyclization of alkynyl aldehyde acetals: Experimental and computational studies
Xu, Tongyu,Yang, Qin,Li, Dongpo,Dong, Jinhua,Yu, Zhengkun,Li, Yuxue
supporting information; experimental part, p. 9264 - 9272 (2010/10/03)
FeCl3·6H2O-and FeBr3-catalyzed Prins cyclization/halogenation of alkynyl aldehyde acetals has been realized with acetyl chloride or bromide as halogen source in dichloromethane to afford 2-(1-halobenzylidene or alkylidene)
