- Enantioselective Michael addition of malonic esters to benzalacetophenone by using chiral phase transfer catalysts derived from proline-mandelic acid/tartaric acid
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Abstract: Herein, we have explored the enantioselective Michael addition of various malonate esters to benzalacetophenone by successful utilization of chiral phase transfer catalysts derived from proline, mandelic acid and tartaric acid under mild phase t
- Mahajan, Deepak P,Godbole, Himanshu M,Singh, Girij P,Shenoy, Gautham G
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- Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction
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The enantioselective Michael addition of dimethyl malonate to 1,3-diphenylprop-2-en-1-one promoted by a quaternary derived ammonium salt from quinine as a phase transfer catalyst in different ionic liquids, 1-butyl-3-methyl imidazolium hexafluorophosphate, [bmim]PF6, 1-butyl-3-methyl pyridinium tetrafluoroborate, [bpy]BF4, 1-butyl-3-methyl imidazolium tetrafluoroborate [bmim]BF4 as well as in conventional organic solvents was studied.
- Dere, Ravindra T.,Pal, Ravindra R.,Patil, Prashant S.,Salunkhe, Manikrao M.
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- In vitro antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall
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Here we report the synthesis, in vitro antifungal evaluation and SAR study of 41 chalcones and analogues. In addition, all active structures were tested for their capacity of inhibiting Saccharomyces cerevisiae β(1,3)-glucan synthase and chitin synthase,
- Lopez, Silvia N.,Castelli, Maria V.,Zacchino, Susana A.,Dominguez, Jose N.,Lobo, Gricela,Charris-Charris, Jaime,Cortes, Juan C.G.,Ribas, Juan C.,Devia, Cristina,Rodriguez, Ana M.,Enriz, Ricardo D.
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- Catalysis of the Michael addition reaction by late transition metal complexes of BINOL-derived salens
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Salen metal complexes incorporating two chiral BINOL moieties have been synthesized and characterized by X-ray crystallography. The X-ray structures show that this new class of Ni-BINOL-salen catalysts contains an unoccupied apical site for potential coor
- Annamalai, Venkatachalam,DiMauro, Erin F.,Carroll, Patrick J.,Kozlowski, Marisa C.
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- Enantioselective Michael reaction of malonates and chalcones by phase-transfer catalysis using chiral quaternary ammonium salt
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The catalytic enantioselective Michael reaction promoted by quaternary ammonium salt from cinchonidine as a phase-transfer catalyst is described. Treatment of malonate with chalcone derivatives under mild reaction conditions afforded the corresponding Michael adducts in good yields with good to moderate enantiomeric excesses.
- Kim, Dae Young,Huh, Sun Chul,Kim, Sung Min
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- Asymmetric Michael addition of malonates to unsaturated ketones catalyzed by rare earth metal complexes bearing phenoxy functionalized chiral diphenylprolinolate ligands
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A simple, efficient catalytic asymmetric Michael addition of malonates to unsaturated ketones has been successfully developed. This process was promoted by rare earth metal complexes 1–4 bearing a chiral phenoxy functionalized prolinol ligand at room temperature [L1RE(L1H) (H2L1?=?(S)-2,4-di-tert-butyl-6-((2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)phenol, RE?=?Yb 1, Y 2, Sc 3 and L2Sc(L2H) 4 (H2L2?=?(S)-2,4-di-dimethylbenzyl-6-((2-(hydroxydiphenylmethyl)-pyrrolidin-1-yl)methyl)phenol)]. Complex 3 was the best catalyst in the transformation and the products were obtained in up to 99% yield and with 90% ee. In addition, the molecular structures of the catalysts were well characterized, including X-ray determination of complex 3.
- Qian, Qinqin,Zhu, Wenguo,Lu, Chengrong,Zhao, Bei,Yao, Yingming
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supporting information
p. 911 - 917
(2016/09/13)
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- Enantioselective Michael Addition of Malonates to Chalcone Derivatives Catalyzed by Dipeptide-derived Multifunctional Phosphonium Salts
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Highly enantioselective Michael addition of malonates to enones catalyzed by dipeptide-derived multifunctional phosphonium salts has been developed. The newly established catalytic system was characterized with its wide substrate scope featured with aliphatic aldehyde-derived enones and substituted malonates. The gram scale-up synthesis of adducts can also be successfully achieved under optimal conditions with both excellent yield and enantioselectivity.
- Cao, Dongdong,Fang, Guosheng,Zhang, Jiaxing,Wang, Hongyu,Zheng, Changwu,Zhao, Gang
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p. 9973 - 9982
(2016/11/02)
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- Michael Addition of Soft Carbon Nucleophiles to Alkylidene Isoxazol-5-ones: A Divergent Entry to β-Branched Carbonyl Compounds
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A novel, divergent strategy toward the synthesis of β-branched (and linear) carbonyl compounds is developed by taking advantage of alkylidene isoxazol-5-ones as key building blocks. The yields obtained range from good to excellent, therefore making the described methods attractive options for building such molecules. (Chemical Equation).
- Capreti, Naylil M. R.,Jurberg, Igor D.
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p. 2490 - 2493
(2015/05/27)
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- Asymmetric CONJUGATE ADDITION of MALONATE ESTERS to α,β- UNSATURATED N-sulfonyl imines: An expeditious route to chiral δ-aminoesters and piperidones
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The asymmetric conjugate addition of malonate esters to α,β-unsaturated N-sulfonyl imines is catalyzed by PyBOX/La(OTf) 3 complexes in the presence of 4A? MS. The reaction gives the corresponding E enamines bearing a stereogenic center at the allylic position with good yields and enantiomeric ratios up to 97:3. This reaction provides a synthetic entry to chiral δ-aminoesters and piperidones. Copyright
- Espinosa, Miguel,Blay, Gonzalo,Cardona, Luz,Pedro, José R.
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supporting information
p. 14861 - 14866
(2013/11/06)
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- Rasta resin as support for TBD in base-catalyzed organic processes
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Although its intriguing features, such as uniform functionalization through the entire beads and a very high-loading capacity are suitable candidates for solid-phase synthesis and reagent-scavenging, the use of Rasta resin as support for organocatalysis has been little explored. In this contribution, Rasta polymer has been used to preparation of high-loading Rasta-TBD. This catalyst has been able to efficiently promote several organic transformations with constantly good and promising results.
- Bonollo, Simona,Lanari, Daniela,Angelini, Tommaso,Pizzo, Ferdinando,Marrocchi, Assunta,Vaccaro, Luigi
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experimental part
p. 216 - 222
(2012/03/08)
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- Study on the Pd/C-catalyzed (retro-)Michael addition reaction of activated methylene compounds to electron-poor styrenes
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Palladium on carbon (10 % Pd/C) efficiently catalyzes the (retro-)Michael addition of activated methylene compounds 2a-d, such as malononitrile (2b), to mono- and doubly activated styrenes 1a-h to give the adducts 3a-l. The scope and limitations are described. The Knoevenagel condensation reaction of benzaldehyde and 2b or ethyl cyanoacetate (2c) is also catalyzed by 10 % Pd/C. In these cases the Michael adducts can even be prepared in a three-component reaction. A mechanism, with as first step the oxidative addition of 2a-d to Pd0, is proposed. Palladium on carbon (10 % Pd catalyzes the (retro-)Michael addition of activated methylene compounds 2a-d to mono- anddoubly activated styrenes. The scope and limitations of the reaction are described. A mechanism is proposed. Copyright
- Nikishkin, Nicolai I.,Huskens, Jurriaan,Verboom, Willem
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body text
p. 6820 - 6823
(2011/02/26)
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- Water-compatible iminium activation: Highly enantioselective organocatalytic michael addition of malonates to α,β-unsaturated enones
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The highly enantioselective Michael addition of malonates to α,β-unsaturated ketones in water was reported to be catalyzed by a primary-secondary diamine catalyst containing a long alkyl chain. This asymmetric Michael addition process was found to be effe
- Mao, Zhifeng,Jia, Yaomei,Li, Wenyi,Wang, Rui
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supporting information; experimental part
p. 7428 - 7430
(2011/02/22)
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- Organocatalytic enantioselective Michael additions of malonates to 2-cyclopentenone
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The Michael reaction of a dialkyl malonate with a cyclic enone using a chiral diamine-acid combination catalyst gave the desired Michael adduct in high yield with excellent enantiomeric excess in a protic solvent such as methanol and ethanol. The methanol
- Mase, Nobuyuki,Fukasawa, Maho,Kitagawa, Norihiko,Shibagaki, Fumiya,Noshiro, Naoyasu,Takabe, Kunihiko
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scheme or table
p. 2340 - 2344
(2010/11/04)
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- Highly enantioselective michael addition of malonate derivatives to enones catalyzed by an N,N'-dioxide-scandium(III) complex
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A highly enantioselective Michael addition of malonate derivatives to chalcone derivatives catalyzed by L-Ramipril acid derived N,N'-dioxide-scandium (III) complex was reported. The experiment included use of L-Ramipril acid derived N,N'-dioxide L1-nickle(II) complex to catalyze the asymmetric Michael addition of diethyl malonate to chalcone in EtOH at 35°C. The results show that 4 A molecular sieves when added as additives result in an improved reactivity and a 95% yield without loss of enantioselectivity. Diisopropyl malonate is found to be an excellent Michael donor than the reaction accomplished in 15hr in 98% yield with 99% ee. The results also show that the electronic nature or the position of the substituents at the aromatic rings of R2 or 3 has little influence on the enantioselectivity.
- Chen, Donghui,Chen, Zhenling,Xiao, Xiao,Yang, Zhigang,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
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supporting information; experimental part
p. 6807 - 6810
(2010/02/28)
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- Strontium-catalyzed highly enantioselective Michael additions of malonates to enones
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A novel catalyst system based on a chiral strontium complex which promotes the catalytic asymmetric Michael addition reactions of malonates to enones has been developed. The conjugate addition reactions proceeded smoothly in the presence of 5 mol % of the
- Agostinho, Magno,Kobayashi, Shu
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p. 2430 - 2431
(2008/09/19)
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- Chiral bisphosphazides as dual basic enantioselective catalysts
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Chiral bisphosphazides complexed with lithium salts efficiently catalyze the direct enantioselective 1,4-addition of dialkyl malonates to acyclic enones. Spectroscopic studies on the stoichiometry of the bisphosphazide and lithium salt have indicated the
- Naka, Hiroshi,Kanase, Nobuhiko,Ueno, Masahiro,Kondo, Yoshinori
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experimental part
p. 5267 - 5274
(2009/05/26)
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- Michael additions of methylene active compounds to chalcone in ionic liquids without any catalyst: The peculiar properties of ionic liquids
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Michael additions of malonodinitrile as well as several other reagents to chalcone have been found to proceed well in pure ionic liquids, without the addition of any catalyst. The catalytic effect of the residual acidity caused by hydrolysis of ionic liqu
- Meciarova, Maria,Toma, Stefan
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p. 1268 - 1272
(2007/10/03)
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- Asymmetric Michael addition of malonates to enones catalyzed by nanocrystalline MgO
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Highly enantioselective Michael addition of malonates to cyclic and acyclic enones has been achieved by using nanocrystalline magnesium oxide at -20 °C.
- Kantam, M. Lakshmi,Ranganath, Kalluri V.S.,Mahendar, Koosam,Chakrapani, Lakkoju,Choudary
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p. 7646 - 7649
(2008/03/14)
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- Layered double hydroxides-supported diisopropylamide: Synthesis, characterization and application in organic reactions
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The layered double hydroxides-supported diisopropylamide (LDH-DA) catalyst is found to be an efficient and selective solid base for aldol, Knoevenagel, Henry, Michael, transesterification and epoxidation reactions under liquid phase conditions. LDH-DA is synthesized by the interaction of lithium diisopropylamide with LDH-NO3 (as-synthesized) and calcined LDH-NO3. The LDH-DA (Mg/Al, 3/1) and their precursors are well characterized by using various instrumental techniques such as FT-IR, TGA and DTA, powder XRD, solid state 27Al MAS NMR spectroscopy, SEM and XPS (ESCA).
- Kantam, M. Lakshmi,Ravindra,Reddy, Ch. Venkat,Sreedhar,Choudary
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p. 569 - 578
(2007/10/03)
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- Organocatalytic enantioselective conjugate additions to enones
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Conjugate addition reactions of a wide range of nucleophilic enol species with enones, catalyzed by a cinchona alkaloid derived thiourea organocatalyst, have been developed with attending good yields and high enantioselectivities under a mild reaction con
- Wang, Jian,Li, Hao,Zu, Liansuo,Jiang, Wei,Xie, Hexin,Duan, Wenhu,Wang, Wei
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p. 12652 - 12653
(2008/02/05)
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- 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzed Michael reactions
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1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), a bicyclic guanidine base, has been found to be an excellent catalyst for Michael and Michael-type reactions. A wide variety of Michael donors and acceptors can participate in these reactions using 10-20 mol % of
- Ye, Weiping,Xu, Junye,Tan, Chin-Tong,Tan, Choon-Hong
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p. 6875 - 6878
(2007/10/03)
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- New chiral imidazolinic derivatives
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Novel C-2 substituted 4,5-dihydroimidazoles and imidazoles bearing an N-linked stereogenic group were rapidly prepared from a chiral primary amine. Quaternization of these derivatives resulted in a range of scalemic room temperature ionic liquids. The abi
- Genisson, Yves,Lauth-De Viguerie, Nancy,Andre, Chantal,Baltas, Michel,Gorrichon, Liliane
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p. 1017 - 1023
(2007/10/03)
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- Importance of chiral phase-transfer catalysts with dual functions in obtaining high enantioselectivity in the Michael reaction of malonates and chalcone derivatives
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(Chemical Equation Presented) Highly enantioselective Michael addition of diethyl malonate to chalcone derivatives has been achieved under mild phase-transfer conditions by the successful utilization of N-spiro C 2-symmetric chiral quaternary a
- Ooi, Takashi,Ohara, Daisuke,Fukumoto, Kazuhiro,Maruoka, Keiji
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p. 3195 - 3197
(2007/10/03)
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- Enantioselective Michael reaction of ketone lithium enolates using a chiral ligand
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The enantioselective Michael reaction of ketone lithium enolates using a chiral amine ligand (1) was studied. Michael adducts (4) of up to 94% ee were obtained by the reaction between methyl ketones (2) and Michael acceptors (3) having a benzylidene group.
- Yasuda, Kosuke,Shindo, Mitsuru,Koga, Kenji
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p. 6343 - 6346
(2007/10/03)
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- The first heterobimetallic multifunctional asymmetric catalyst
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The optically active lanthanum - sodium - BINOL complex (LSB), prepared from La(O-i-Pr)3, (R)-BINOL (3 mol equiv), and NaO-t-Bu (3 mol equiv), is quite effective as an asymmetric catalyst for various Michael reactions to give adducts in up to 9
- Sasai, Hiroaki,Arai, Takayoshi,Satow, Yoshinori,Houk,Shibasaki, Masakatsu
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p. 6194 - 6196
(2007/10/02)
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- η6-Benzenetricarbonylchromium analogues of chalcones
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Synthesis of 11 η6-benzenetricarbonylchromium analogues of chalcones, starting from the appropriately substituted η6-benzaldehydetricarbonylchromium as well as substituted η6-acetophenonetricarbonylchromium complexes is described.Dimethylmalonate addition to the chalcone and its Cr(CO)3 complex takes place with the same regioselectivity.
- Federic, Jozef,Toma, Stefan,Gautheron, Bernard
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p. 211 - 216
(2007/10/02)
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- Asymmetric Michael Additions via SAMP-/RAMP-Hydrazones Enantioselective 1,4-Addition of Methyl Ketones to Knoevenagel Acceptors
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Asymmetric Michael addition of lithiated methyl ketone SAMP-hydrazones (S)-2 to 2-benzylidenemalonates and -dinitriles 3 followed by oxidative cleavage of the 1,4-adducts (SR)-4 by ozonolysis affords 2-substituted 4-oxo diesters and -dinitriles (R)-5 in good overall yields of 50-82percent and high enantiomeric excesses (ee >/= 95percent).
- Enders, Dieter,Demir, Ayhan S.,Rendenbach, Beatrice E. M.
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p. 1731 - 1736
(2007/10/02)
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