105213-31-8Relevant articles and documents
Iodine mediated a simple strategy for the synthesis of β,γ-unsaturated-α-ketoesters and its application for the synthesis of 4,5-dihydropyrazole derivatives
Pommidi, Anil,Shaik, Asha Begum,Chatterjee, Anindita,Somarapu, Vijaya Laxmi
, p. 1545 - 1553 (2020)
Abstract: Novel and efficient method for the synthesis of a series of β,γ-unsaturated-α-ketoesters under mild conditions was developed. This one-step protocol was achieved by the reaction of electron-rich aromatic aldehydes and pyruvates in the presence o
Stereoselective Organocatalytic Construction of Spiro Oxindole Pyrrolidines Using Unsaturated α-Ketoesters and α-Ketoamides
Peňa?ka, Tibor,Palchykov, Vitalii,Rakovsky, Erik,Addová, Gabriela,?ebesta, Radovan
supporting information, p. 1693 - 1703 (2021/03/15)
We have investigated the stereoselective formation of spiro oxindole pyrrolidines via formal [3+2] cycloaddition of oxindole imines with ketoesters and ketoamides. Bifunctional squaramide organocatalyst was able to induce enantioselectivity of up to 60 %
Facile synthesis of substituted diaryl sulfones: Via a [3 + 3] benzannulation strategy
Tang, Xiang-Zheng,Tong, Lang,Liang, Hua-Ju,Liang, Jie,Zou, Yong,Zhang, Xue-Jing,Yan, Ming,Chan, Albert S. C.
supporting information, p. 3560 - 3563 (2018/05/26)
A base-mediated [3 + 3] benzannulation strategy for the conversion of 1,3-bis(sulfonyl)propenes and β,γ-unsaturated α-ketoesters to diaryl sulfones has been developed. This method provides facile, metal-free and efficient access to highly substituted diaryl sulfones in good to excellent yields. In addition, the sulfonyl group could be easily removed or converted to other functional groups via an organostannane intermediate.
Catalytic Generation of Donor-Acceptor Cyclopropanes under N-Heterocyclic Carbene Activation and their Stereoselective Reaction with Alkylideneoxindoles
Prieto, Liher,Sánchez-Díez, Eduardo,Uria, Uxue,Reyes, Efraím,Carrillo, Luisa,Vicario, Jose L.
, p. 1678 - 1683 (2017/05/22)
Formylcyclopropanes undergo activation in the presence of an N-heterocyclic carbene catalyst generating a donor-acceptor cyclopropane intermediate with the ability to undergo ring-opening followed by formal [4+2] cycloaddition with alkylideneoxindoles. This enables the direct enantio- and diastereoselective synthesis of tetrahydropyrano[2,3-b]indoles through the use of a chiral NHC catalyst. (Figure presented.).
Boosting Chemical Stability, Catalytic Activity, and Enantioselectivity of Metal-Organic Frameworks for Batch and Flow Reactions
Chen, Xu,Jiang, Hong,Hou, Bang,Gong, Wei,Liu, Yan,Cui, Yong
, p. 13476 - 13482 (2017/10/05)
A key challenge in heterogeneous catalysis is the design and synthesis of heterogeneous catalysts featuring high catalytic activity, selectivity, and recyclability. Here we demonstrate that high-performance heterogeneous asymmetric catalysts can be engineered from a metal-organic framework (MOF) platform by using a ligand design strategy. Three porous chiral MOFs with the framework formula [Mn2L(H2O)2] are prepared from enantiopure phosphono-carboxylate ligands of 1,1′-biphenol that are functionalized with 3,5-bis(trifluoromethyl)-, bismethyl-, and bisfluoro-phenyl substituents at the 3,3′-position. For the first time, we show that not only chemical stability but also catalytic activity and stereoselectivity of the MOFs can be tuned by modifying the ligand structures. Particularly, the MOF incorporated with -CF3 groups on the pore walls exhibits enhanced tolerance to water, weak acid, and base compared with the MOFs with -F and -Me groups. Under both batch and flow reaction systems, the CF3-containing MOF demonstrated excellent reactivity, selectivity, and recyclability, affording high yields and enantioselectivities for alkylations of indoles and pyrrole with a range of ketoesters or nitroalkenes. In contrast, the corresponding homogeneous catalysts gave low enantioselectivity in catalyzing the tested reactions.
Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters
Taylor, James E.,Davies, Alyn T.,Douglas, James J.,Churchill, Gwydion,Smith, Andrew D.
, p. 355 - 366 (2017/02/15)
N-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of α-aroyloxyaldehydes with either β,γ-unsaturated α-ketoesters or α,β-unsaturated γ-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained.
A New Strategy for Enantioselective Construction of Multisubstituted Five-Membered Oxygen Heterocycles via a Domino Michael/Hemiketalization Reaction
Hua, Yuan-Zhao,Liu, Meng-Meng,Huang, Pei-Jin,Song, Xixi,Wang, Min-Can,Chang, Jun-Biao
supporting information, p. 11994 - 11998 (2015/08/18)
A new highly enantioselective domino Michael/hemiketalization reaction of α-hydroxyacetophenone with β,γ-unsaturated α-keto esters for the synthesis of 2,2,4,5-tetrasubstituted chiral tetrahydrofurans is reported. With 2 mol% intramolecular dinuclear zinc
Synthesis of functionalized 2,5-dihydro-1,2-oxaphospholes via one-pot three-component reaction
Balalaie, Saeed,Baoosi, Leila,Tahoori, Fatemeh,Rominger, Frank,Bijanzadeh, Hamid Reza
, p. 101 - 105 (2015/01/30)
An efficient one-pot synthesis of novel 2,5-dihydro-1,2-oxaphosphole derivatives via a three-component reaction of triphenyl phosphine, dialkyl acetylenedicarboxylates, and methyl (arylmethylidene) pyruvates has been reported. Carrying out the reaction in
Aryl butenoic acid derivatives as a new class of histone deacetylase inhibitors: Synthesis, in vitro evaluation, and molecular docking studies
Esiyok, Peruze Ayhan,Seven, Ozlem,Eymur, Gueluezar,Tatar, Gamze Bora,Erden, Didem Dayangac,Yelekci, Kemal,Yurter, Hayat,Demir, Ayhan Sitki
, p. 338 - 344 (2014/04/03)
New aryl butenoic acid derivatives have been synthesized by combining hydroxy- or methoxy-substituted phenyl rings as the capping group, with a double bond in the short linker as well as metal binding groups, enoic ester, and salts bearing either methyl o
Synthesis of polysubstituted 1,4-dihydropyridines via three-component reaction
Balalaie, Saeed,Baoosi, Leila,Tahoori, Fatemeh,Rominger, Frank,Bijanzadeh, Hamid Reza
, p. 738 - 743 (2013/07/27)
An efficient one-pot synthesis of novel N-substituted 1,4-dihydropyridine derivatives via a threecomponent reaction of primary amines, dialkyl acetylenedicarboxylates, and methyl (arylmethylidene) pyruvates has been reported. The reaction is performed using ZnCl2 (40 mol %) in dichloroethane in good to high yields through a domino Michael/cyclization sequence. Notably, the ready availability of the starting materials, high bond-forming efficiency, good to high yields and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to Nsubstituted 1,4-dihydropyridines.
