- Synthesis of a New N-Diaminophosphoryl-N'-[(2S)-2-pyrrolidinylmethyl]thiourea as a Chiral Organocatalyst for the Stereoselective Michael Addition of Cyclohexanone to Nitrostyrenes and Chalcones – Application in Cascade Processes for the Synthesis of Polyc
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A highly diastereoselective and enantioselective Michael addition of enolizable ketones such as cyclohexanone and acetophenone to a variety of substituted trans-?-nitrostyrenes and chalcones was catalyzed by a novel chiral and unsymmetrical thiourea as or
- Cruz-Hernández, Carlos,Martínez-Martínez, Eduardo,Hernández-González, Perla E.,Juaristi, Eusebio
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supporting information
p. 6890 - 6900
(2018/11/23)
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- A chiral benzoylthiourea-pyrrolidine catalyst for the highly enantioselective Michael addition of ketones to chalcones
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A benzoylthiourea-pyrrolidine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding products were obtained in high yields with high level of diastereoselectivities (up to 99:1 dr) and high level of enantioselectivities (up to 94% ee) under mild conditions.
- Ban, Shu-Rong,Zhu, Xi-Xia,Zhang, Zhi-Ping,Li, Qing-Shan
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supporting information
p. 2517 - 2520
(2014/05/20)
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- Direct asymmetric Michael addition of ketones to chalcones catalyzed by a hydroxyphthalimide derived triazole-pyrrolidine
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An efficient protocol for the enantioselective Michael additions of ketones to chalcones catalyzed by a hydroxyphthalimide linked triazole-pyrrolidine derivative has been developed. The corresponding products, 1,5-dicarbonyl compounds, were obtained in good yields with high levels of stereoselectivities under mild reaction conditions employing benzoic acid as an additive.
- Kumar, Togapur Pavan,Sattar, Mohammad Abdul,Sarma, Vanka Uma Maheshwara
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p. 1615 - 1619
(2014/01/06)
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- Highly enantioselective Michael addition of cyclic ketones to chalcones catalyzed by pyrrolidine-based imides
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An efficient procedure for asymmetric Michael addition reaction of cyclic ketones with low activated chalcones catalyzed by pyrrolidine-based phthalimide and 1,8-Naphthalimide catalysts was developed. The corresponding products were obtained in high yield
- Xie, Hong-Yu,Ban, Shu-Rong,Liu, Ju-Na,Li, Qing-Shan
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supporting information; experimental part
p. 3865 - 3868
(2012/08/14)
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- Synthesis of novel N-hydroxy heterocycles via intramolecular reductive cyclization of diketoximes by NaBH3CN
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A simple and efficient protocol for the construction of substituted piperazines, piperidines, thiomorpholines, decahydroquinolines, perhydrocyclopenta[b]pyridine, and pyrrolidines bearing N-hydroxy substituents through intramolecular reductive cyclization of diketoximes using sodium cyanoborohydride is described.
- Nagaraj, Muthupandi,Boominathan, Muthusamy,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
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body text
p. 4642 - 4652
(2011/07/29)
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- Three-step synthesis of 2,4-diaryl-5,6,7,8-tetrahydroquinoline derivatives
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(Chemical Equation Presented) Addition of cylohexanone to chalcones, obtained from the appropriate acetophenone and benzaldehyde derivatives, under solvent-free conditions gave 1,5-diketones in good yields. Treatment of 1,5-diketones with ammonium acetate in acetic acid afforded directly 2,4-diaryl-5,6,7,8-tetrahydroquinoline derivatives (7a-u) in high yields. The structures of 7a-u were elucidated by 1H NMR, 13C NMR, IR, and elemental analysis.
- Gezegen, Hayreddin,Dingil, Alparslan,Ceylan, Mustafa
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experimental part
p. 1017 - 1024
(2010/10/21)
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- A mild and efficient procedure for asymmetric Michael additions of cyclohexanone to chalcones catalyzed by an amino acid ionic liquid
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A mild and efficient procedure for Michael additions of cyclohexanone to chalcones has been developed. In the presence of amino acid ionic liquid [EMIm][Pro] (200 mol %), cyclohexanone reacted with various chalcones to afford Michael adducts in high yield
- Qian, Yunbo,Xiao, Shiyong,Liu, Lei,Wang, Yongmei
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p. 1515 - 1518
(2008/12/21)
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- Chemiluminescent 1,2-dioxetanes
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A method of generating light through chemiluminescence involves providing a stable 1,2-dioxetane of the formula: Wherein (a) R1 and R2 are each, individually, a chemical reactive site or when fused together form a chemical reactive site, and R3 and R4 are each, individually, a chemical reactive site or when fused together form a chemical reactive or (b) R1 has at least two hetero atoms with chemical reactive site and R3 and R4 are inactive site and R2 is a chemical reactive site.
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- Lewis base-catalyzed Michael reactions between trimethylsilyl enolate and α,β-unsaturated carbonyl compounds
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Michael reactions between trimethylsilyl enolates and α,β- unsaturated carbonyl compounds by using a Lewis base catalyst such as lithium benzamide 4 or lithium succinimide 5 in DMF proceeded smoothly to afford the corresponding Michael-adducts in good to high yields (Tables 1-3). In order to extend the scope, Michael reactions catalyzed by lithium acetate (AcOLi), a weak and readily available Lewis base, were studied in detail. AcOLi behaved as an effective Lewis base catalyst in Michael reactions between trimethylsilyl enolates and α,β-unsaturated carbonyl compounds at 0 °C or at room temperature (Tables 4-6). Hindered α,β-unsaturated ketones behaved as excellent Michael-acceptors in the above reaction at room temperature (Table 5). This catalytic Michael reaction also proceeds smoothly in the presence of other lithium carboxylates that are easily prepared in situ by treating carboxylic acids with lithium carbonate (LE2CO3) (Scheme 2). This is the first example of Lewis base-catalyzed Michael reactions between α,β-unsaturated carbonyl compounds and trimethylsilyl enolates.
- Nakagawa, Takashi,Fujisawa, Hidehiko,Nagata, Yuzo,Mukaiyama, Teruaki
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p. 236 - 246
(2008/02/04)
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- Lithium acetate-catalyzed Michael reaction between trimethylsilyl enolate and α,β-unsaturated carbonyl compound
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Lithium acetate-catalyzed Michael reaction between trimethylsilyl enolates and α,β-unsaturated carbonyl compounds in DMF proceeded smoothly to afford the corresponding Michael-adducts in good to high yields. Hindered α,β-unsaturated ketones also behaved as an excellent Michael-acceptor in the above reaction at room temperature.
- Nakagawa, Takashi,Fujisawa, Hidehiko,Nagata, Yuzo,Mukaiyama, Teruaki
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p. 1016 - 1017
(2007/10/03)
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- Chemiluminescent 1,2-dioxetanes
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A method of generating light through chemiluminescence involves providing a stable 1,2-dioxetane of the formula: Wherein (a) R1 and R2 are each, individually, a chemical reactive site or when fused together form a chemical reactive site, and R3 and R4 are each, individually, a chemical reactive site or when fused together form a chemical reactive or (b) R1 has at least two hetero atoms with chemical reactive site and R3 and R4 are inactive site and R2 is a chemical reactive site.
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- Magnesium Chloride-Promoted Michael Addition of Dimethylsilyl Enolates to α-Enones
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In the presence of MgCl2, dimethylsilyl (DMS) enolates 1 smoothly reacted with α-enones in DMF to form 1,5-diketones 3 in moderate to high yields. The Michael addition proceeded with moderate to high anti-diastereoselectivity.
- Miura, Katsukiyo,Nakagawa, Takahiro,Hosomi, Akira
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p. 2068 - 2070
(2007/10/03)
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- Chemiluminescent 1,2-dioxetanes
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The present invention provides novel 1,2-dioxetanes derived from spiro-fused ketones with or without π-electrons in the ring or with carbon-carbon double bond(s) in the spiro-fused ring. Additionally, these new dioxetanes have electron donating or withdrawing groups at the four-membered peroxide ring to render these dioxetanes active at all sites.
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- Some reactions of hexahydro[1,3,4]oxadiazolo2,3-j|quinolines and pathways of their formation
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Some transformations of 2,5,7-triphenyl-7,7a,8,9,10,11-hexahydro[1,3,4]oxadiazolo[2,3-j]quino-lines and pathways of their formation by reactions of 3-(2-oxocyclohexyl)-1,3-diphenyl-1-propanone with corresponding benzohydrazides were studied. 1-Benzoylamino-2,4-diphenyl-1,4,5,6,7,8-hexahydroquinoline was prepared. In the formation of oxadiazoloquinolines from 3-(2-oxocyclohexyl)-1,3-diphenyl-1-propanone closure of the oxadiazole ring precedes closure of the quinoline system.
- Moskovkina
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p. 1077 - 1081
(2007/10/03)
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- Alkali metal hydride or aqueous hydroxide induced conjugate addition of trimethylsilyl enol ethers to enones. A convenient alternative to Lewis acid mediated reaction
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Conjugate addition to enones by enolates derived from base-induced cleavage of O-Si bond of trimethylsilyl enol ethers, yields 1,5-dicarbonyl compounds in good yields.
- Swamy, Vishwanath M.,Sarkar, Amitabha
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p. 1261 - 1264
(2007/10/03)
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- Kinetics and Mechanisms of Nucleophilic Displacements with Heterocycles as Leaving Groups. 2. N-Benzylpyridinium Cations: Rate Variation with Steric Effects in the Leaving Group
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N-Benzyl groups are transferred to piperidine from pyridinium ions by unimolecular SN1 and/or bimolecular SN2 mechanisms.Steric acceleration by α-phenyl groups is reduced by an adjacent β-methyl group but increased by constraining th
- Katritzky, Alan R.,El-Mowafy, Azzahra M.,Musumarra, Giuseppe,Sakizadeh, Kumars,Sana-Ullah, Choudhry,et al.
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p. 3823 - 3830
(2007/10/02)
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- CATALYSE HETEROGENE PAR DES SELS ET SANS SOLVANT. III. SYNTHESE DE COMPOSES CARBONYLES α,β INSATURES A PARTIR D'ETHERS D'ENOLS SILYLES
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The reactions of silyl enol ethers with carbonyl compounds are activated by heterogeneous catalysis.Caesium fluoride is the best catalyst.Unsaturated ketones are directly obtained by condensation reactions of silyl enol ethers with aldehydes and ketones. 1,4 Addition with α,β-unsaturated carbonyl compounds gives 1,5 dicarbonyl products.This method is very convenient and the compounds obtained can easily be separated.We assume that the role of the salt in these reactions is to activate the silicon atom by anionic coordination to form a pentacoordinated silicon intermediate.
- Boyer, J.,Corriu, R. J. P.,Perz, R.,Reye, C.
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p. 157 - 166
(2007/10/02)
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